CN108752264A - Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device - Google Patents

Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device Download PDF

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CN108752264A
CN108752264A CN201810406967.8A CN201810406967A CN108752264A CN 108752264 A CN108752264 A CN 108752264A CN 201810406967 A CN201810406967 A CN 201810406967A CN 108752264 A CN108752264 A CN 108752264A
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organic electroluminescence
electroluminescence device
layer
carbon
compound
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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, containing unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device and display device more particularly to one kind.Shown in compound according to the present invention such as formula (I)：

Description

Contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, organic electroluminescence device And display device
Technical field
The present invention relates to display technology fields, containing unsaturated nitrogenous heterocyclic dihydroanthracene chemical combination more particularly to one kind Object, 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 (EmittingLayer, abbreviation EML), sky Cave transport layer, hole injection layer, anode and substrate.The raising of organic electroluminescence device efficiency, mainly in organic luminous layer The formation probability of exciton, therefore the organic luminous layer of organic electroluminescence device and hole transport adjacent thereto are inside improved as possible The material of layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And sky in the prior art Cave transport 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 dihydroanthracene compound, includes the organic of the compound Electroluminescent device and display device with the organic electroluminescence device, to solve organic electroluminescent in the prior art The problem of high driving voltage of device and low luminous efficiency.
According to an aspect of the present invention, it provides a kind of containing unsaturated nitrogenous heterocyclic dihydroanthracene compound, the change It closes shown in object such as formula (I)：
Wherein Ar1Undersaturated nitrogen heterocyclic ring, carbon atom 12~40 selected from carbon atoms 3~60 it is undersaturated oxygen-containing The undersaturated sulfur heterocyclic ring of heterocycle, carbon atom 12~40, the Ar1Can by the aliphatic alkyl of carbon atoms 1-30, contain The aliphatic alkoxy of carbon atom 1-30, the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen are replaced.
And Ar1It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen1Direct and dihydro anthracene nucleus On C atoms connection, can also be Ar1Pass through the C on the aromatic radical being made of carbon and hydrogen and dihydro anthracene nucleus of carbon atom 6-40 Atom connects, and is illustrated below：
Work as Ar1Selected from pyridyl group, when the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen is selected from phenyl, Ar1Directly and two When C atoms on hydrogen anthracene nucleus connect, shown in obtained compound such as formula (II)：
Work as Ar1Selected from pyridyl group, when the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen is selected from phenyl, Ar1Pass through carbon original Sub- 6-40's is connected with the aromatic radical that hydrogen forms with the C atoms on dihydro anthracene nucleus by carbon, obtained compound such as formula (III) institute Show：
Further, Ar1It is selected from：Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, triazine radical, benzimidazolyl, hexichol And furyl, benzo benzo furyl, dinaphtho furyl, Ar1Can by methyl, ethyl, propyl, butyl, amyl, hexyl, Heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, ethyoxyl, the third oxygen Base, butoxy, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, penta oxygen of ring Base, cyclohexyloxy, two cyclohexyloxies, phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene substitution；The fat of carbon atom 1-30 Fat race alkyl is selected from：Methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, Cyclopenta, cyclohexyl, dicyclohexyl；The aliphatic alkoxy of carbon atoms 1-30 is selected from：Methoxyl group, ethyoxyl, propoxyl group, fourth Oxygroup, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, cyclobutoxy group, cyclopentyloxy, ring Hexyloxy, two cyclohexyloxies；The aromatic radical of carbon atom 6-40 being made of carbon and hydrogen is selected from：Phenyl, xenyl, naphthalene, anthryl, It is phenanthryl, triphenylene, 9,9- dimethyl fluorenyl, 9,9- diphenyl amyl, Spirofluorene-based.
In addition, the present invention's contains unsaturated nitrogenous heterocyclic dihydroanthracene compound, Ar1It can be by carbon atoms 1-30 Aliphatic alkyl, carbon atoms 1-30 aliphatic alkoxy replaced, wherein the substitution, can be monosubstituted, double take Generation or it is polysubstituted.
Optionally, according to the present invention to be selected from containing unsaturated nitrogenous heterocyclic dihydroanthracene compound：
It should be noted that in concrete structure listed above, the connection type of adjacent group is unique, such as in P- In 50, the phenyl ring contraposition connected on dihydro anthracene nucleus is replaced by dibenzofurans, in fact, between the phenyl ring connected on dihydro anthracene nucleus Position by dibenzofurans replace and dihydro anthracene nucleus on the ortho position of phenyl ring that connects replaced by dibenzofurans and be formed by chemical combination Object, 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, Ar1The change of connection type, belongs to the present invention between representative inside configuration difference or identical group Disclosure and protection within the scope of.
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 contain unsaturated nitrogenous heterocyclic dihydroanthracene compound.
Optionally, the material of main part of the organic luminous layer of the organic electroluminescence device or/and electron transport material To contain unsaturated nitrogenous heterocyclic 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：
Electron transfer layer or/and organic luminous layer by compound provided by the invention for organic electroluminescence device Material of main part, improve the luminous efficiency of organic electroluminescence device, reduce 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
In 500 milliliters of there-necked flask, under nitrogen protection, 200 milliliters of dry dimethyl sulfoxide (DMSO)s of addition, 1.8 grams Under stirring, the sodium hydride of 3.2 grams of (0.08mol) contents 60% is added portionwise in (0.01mol) 9,10- dihydroanthracenes, in 30 DEG C of stirrings 30 minutes, 14.04 grams of (0.06mol) 2- phenyl -5- bromopyridines are added, 60 DEG C is warming up to and reacts 1 hour, then be warming up to 80 DEG C Reaction 1 hour, then be warming up to 120 DEG C and react 1 hour, it reheats to 160 DEG C and reacts 8 hours, be down to room temperature, a small amount of methanol point is added Excessive sodium hydride is solved, ammonium chloride solution is then added, is filtered, obtained solid washing, methanol washing, then with silicagel column point From using petroleum ether：Ethyl acetate (volume ratio 3：1) it is eluted as eluant, eluent, obtains product 2.58 shown in formula P-1 Gram, yield 32.6%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：792.
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 8.21 (m, 8H), δ 8.17 (d, 4H), δ 7.60 (d, 4H), δ 7.50~7.36 (m, 12H), δ 7.18 (m, 4H), δ 7.13~6.99 (m, 8H).
Elemental analysis carried out to obtained compound P-1, and measured value % (C, 87.68；H, 5.10；N, 7.06), calculate Value (C, 87.85；H,5.08；N,7.07).
The synthesis of other parts compound of the present invention
Synthetic method with reference to P-1 synthetic method, only according to needing to change 2- phenyl -5- bromopyridines therein accordingly into Bromo-derivative has carried out Mass Spectrometer Method to obtained compound, and the raw material and product Mass Spectrometer Method result used in building-up process are shown in Following table：
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 or electron transport material of organic luminous 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
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
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 dihydroanthracene compound, as shown in formula (I)：
Wherein Ar1Undersaturated nitrogen heterocyclic ring selected from carbon atoms 3~60, the Ar1It can be by the fat of carbon atoms 1-30 Race's alkyl, the aliphatic alkoxy of carbon atoms 1-30, carbon atom 6-40 the aromatic radical being made of carbon and hydrogen replaced, and Ar1It, can be with Ar when being replaced by the aromatic radical of carbon atom 6-40 being made of carbon and hydrogen1C atoms directly and on dihydro anthracene nucleus connect It connects, can also be Ar1It is connected with the C atoms on dihydro anthracene nucleus with the aromatic radical that hydrogen forms by carbon by carbon atom 6-40.
2. it is according to claim 1 containing unsaturated nitrogenous heterocyclic dihydroanthracene compound,
Wherein Ar1It is selected from：Pyridyl group, quinolyl, isoquinolyl, pyrimidine radicals, the Ar1It can be by methyl, ethyl, propyl, fourth Base, amyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl, dicyclohexyl, methoxyl group, Ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, octyloxy, nonyl epoxide, decyloxy, ring propoxyl group, ring fourth Oxygroup, cyclopentyloxy, cyclohexyloxy, two cyclohexyloxies, phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene substitution.
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 6-40 being made of carbon and hydrogen is selected from：Phenyl, xenyl, naphthalene, anthryl, phenanthryl, triphenylene, It is 9,9- dimethyl fluorenyls, 9,9- diphenyl amyl, Spirofluorene-based.
3. according to claim 1 contain unsaturated nitrogenous heterocyclic dihydroanthracene compound, Ar1It can be by carbon atoms The aliphatic alkyl of 1-30, the aliphatic alkoxy of carbon atoms 1-30 are replaced, wherein the substitution, can be it is monosubstituted, It is disubstituted or polysubstituted.
4. it is according to claim 1 containing unsaturated nitrogenous heterocyclic dihydroanthracene compound, 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 Described contains unsaturated nitrogenous heterocyclic 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/and the material of electron transfer layer are described in claim 1-4 is any containing unsaturated nitrogenous The dihydroanthracene compound of heterocycle.
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.
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Citations (1)

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Publication number Priority date Publication date Assignee Title
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* 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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