CN109721540A - Dihydrobenzo indazole compounds, organic electroluminescence device and display device - Google Patents
Dihydrobenzo indazole compounds, organic electroluminescence device and display device Download PDFInfo
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- CN109721540A CN109721540A CN201811548632.6A CN201811548632A CN109721540A CN 109721540 A CN109721540 A CN 109721540A CN 201811548632 A CN201811548632 A CN 201811548632A CN 109721540 A CN109721540 A CN 109721540A
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Abstract
The present invention relates to field of display technology, more particularly to a kind of dihydrobenzo indazole compounds, organic electroluminescence device and display device.Shown in compound according to the present invention such as formula (A):Wherein, Ar1To Ar6Be each independently selected from substituted or unsubstituted C6~C60 is free of heteroatomic aryl.
Description
Technical field
The present invention relates to field of display technology, send out more particularly to a kind of dihydrobenzo indazole compounds, organic electroluminescence
Optical device and display device.
Background technique
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) is put down as novel
Plate display is compared with liquid crystal display (Liquid Crystal Display, abbreviation LCD), has thin, light, wide viewing angle, master
It is dynamic shine, luminescent color is continuously adjustable, at low cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, gives birth to
Production. art is simple, luminous efficiency is high and can Flexible Displays the advantages that, obtained the very big concern of industrial circle and scientific circles.
The development of organic electroluminescence device promotes research of the people to electroluminescent organic material.Relative to inorganic hair
Luminescent material, electroluminescent organic material have the advantage that organic material processing performance is good, can pass through vapor deposition or the side of spin coating
Method forms a film on any substrate；The diversity of organic molecular structure allow to by Molecular Design and the method for modification come
Adjust thermal stability, mechanical performance, the luminous and electric conductivity of organic material, the space so that material is significantly improved.
What the generation of organic electroluminescent was leaned on is the carrier (electrons and holes) transmitted in organic semiconducting materials
Recombination.It is well known that the electric conductivity of organic material is very poor, there is no the energy band continued in organic semiconductor, the transmission of carrier is normal
It is described with jump theory.In order to make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material
The difficulty of charge injection and transmittability difference.Scientists are by the adjustment of device architecture, such as increase device organic material layer
Number, and so that different organic layers is played the part of different device layers, such as the functional material having can promote electronics from cathode
Injection, some functional materials can promote hole to inject from anode, and some materials can promote the transmission of charge, and some materials are then
It can play the role of stopping electronics or hole transport, the hair of most important various 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 service life length
Usually device architecture and various organic materials optimization collocation as a result, this is just that chemists design and develop various structures
Functionalization material provides great opportunities and challenges.
Existing organic electroluminescence device generally comprises the cathode, electron injecting layer, electronics being arranged successively 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 far as possible, therefore the organic luminous layer of organic electroluminescence device and hole adjacent thereto pass
The material of defeated layer and hole injection layer plays the role of the luminous efficiency of organic electroluminescence device and brightness vital.And
The material of hole transmission layer or hole injection layer in the prior art makes organic electroluminescence device driving voltage with higher
With lower luminous efficiency.
Summary of the invention
The present invention provides a kind of dihydrobenzo indazole compounds, the organic electroluminescence device comprising the compound and
Display device with the organic electroluminescence device, to solve the high driving electricity of organic electroluminescence device in the prior art
The problem of pressure and low luminous efficiency.
According to an aspect of the present invention, a kind of dihydrobenzo indazole compounds, the compound such as formula (A) institute are provided
Show:
Wherein, Ar1To Ar6Be each independently selected from substituted or unsubstituted C6~C60 is free of heteroatomic aryl.
According to embodiment of the present invention, the C6~C60 without heteroatomic aryl be selected from phenyl, naphthalene,
Anthryl, phenanthryl, cyclopentaphenanthreneyl, two fluorenyl of spiral shell, pyrenyl, triphenylene, fluoranthene base, indeno fluorenyl, xenyl, terphenyl,
Fluorenyl, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl or benzo anthryl.
According to embodiment of the present invention, Ar1And Ar2At least one of for replace C6~C60 be free of miscellaneous original
The aryl of son, substituent group are each independently selected from: at least one in the naphthenic base and phenyl of the alkyl of C1~C20, C3~C20
Kind.
According to embodiment of the present invention, Ar3To Ar6At least one of for replace C6~C60 be free of miscellaneous original
The aryl of son, substituent group are each independently selected from: the alkyl of C1~C20, the naphthenic base of C3~C20, phenyl, naphthalene, anthryl, phenanthrene
Base, cyclopentaphenanthreneyl, Spirofluorene-based, pyrenyl, triphenylene, fluoranthene base, indeno fluorenyl, xenyl, fluorenyl, benzo fluorenyl, indeno
At least one of anthryl, dibenzo fluorenyl, naphtho- anthryl and benzo anthryl.
According to embodiment of the present invention, the compound of the present invention meets at least one of following three conditions:
(a)Ar1And Ar2It is identical, (b) Ar3And Ar6It is identical, (c) Ar4And Ar5It is identical.
According to embodiment of the present invention, the compound of the present invention is selected from:
According to another aspect of the present invention, the preparation method of dihydrobenzo indazole compounds as described above is provided,
Including dihydrobenzo indazole substituent group corresponding to what is be activated is carried out substitution reaction.
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, which contains
With good grounds dihydrobenzo indazole compounds of the invention.
According to embodiment of the present invention, the hole mobile material of the organic electroluminescence device includes according to this hair
Bright dihydrobenzo indazole compounds.
According to embodiment of the present invention, the hole-injecting material of the organic electroluminescence device includes according to this hair
Bright dihydrobenzo indazole compounds.
According to another aspect of the present invention, a kind of display device is provided, which includes according to the present invention having
Organic electroluminescence devices.
Beneficial effects of the present invention are as follows:
Compound provided by the invention is used for the hole transmission layer or sky of the organic luminous layer of organic electroluminescence device
Cave implanted layer improves the luminous efficiency of organic electroluminescence device, reduces the driving voltage of organic electroluminescence device.
Specific embodiment
Specific embodiment is only the description of the invention, without constituting the limitation to the content of present invention, below in conjunction with
Invention is further explained and description for specific embodiment.
The present invention provides a kind of dihydrobenzo indazole compounds, the organic electroluminescence device comprising the compound and
Display device with the organic electroluminescence device.
According to an aspect of the present invention, a kind of dihydrobenzo indazole compounds, the compound such as formula (A) institute are provided
Show:
Wherein, Ar1To Ar6Be each independently selected from substituted or unsubstituted C6~C60 is free of heteroatomic aryl.
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.
According to embodiment of the present invention, the C6~C60 without heteroatomic aryl be selected from phenyl, naphthalene,
Anthryl, phenanthryl, cyclopentaphenanthreneyl, two fluorenyl of spiral shell, pyrenyl, triphenylene, fluoranthene base, indeno fluorenyl, xenyl, terphenyl,
Fluorenyl, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl or benzo anthryl.
In the present invention, the carbon atom mentioned in " selected from substituted or unsubstituted C6~C60 be free of heteroatomic aryl "
Carbon atom number when C6~C60 refers to not yet being substituted is counted, the carbon atom on substituent group does not count.For other similar
Statement, should also make identical understanding.
According to embodiment of the present invention, Ar1And Ar2It is unsubstituted C6~C60 without heteroatomic virtue
Base.
Another embodiment according to the present invention, Ar1And Ar2At least one of for replace C6~C60 be free of miscellaneous original
The aryl of son, substituent group are each independently selected from: at least one in the naphthenic base and phenyl of the alkyl of C1~C20, C3~C20
Kind.
According to embodiment of the present invention, Ar3To Ar6It is unsubstituted C6~C60 without heteroatomic virtue
Base.
Another embodiment according to the present invention, Ar3To Ar6At least one of for replace C6~C60 be free of miscellaneous original
The aryl of son, substituent group are each independently selected from: the alkyl of C1~C20, the naphthenic base of C3~C20, phenyl, naphthalene, anthryl, phenanthrene
Base, cyclopentaphenanthreneyl, Spirofluorene-based, pyrenyl, triphenylene, fluoranthene base, indeno fluorenyl, xenyl, fluorenyl, benzo fluorenyl, indeno
At least one of anthryl, dibenzo fluorenyl, naphtho- anthryl and benzo anthryl.
According to embodiment of the present invention, the compound of the present invention meets at least one of following three conditions:
(a)Ar1And Ar2It is identical, (b) Ar3And Ar6It is identical, (c) Ar4And Ar5It is identical.
According to embodiment of the present invention, Ar1And Ar2It is identical.
According to embodiment of the present invention, Ar1And Ar2It is identical, Ar3And Ar6It is identical, and Ar4And Ar5It is identical.
According to embodiment of the present invention, Ar1And Ar2It is identical, Ar3、Ar4、Ar5And Ar6It is all the same.
In the present invention, " substituent group is each independently selected from " refers to that substituent group can be same or different, can be independent
Selection.
In the present invention, " alkyl of C1~C20 " further can be the alkyl of C1~C12, the alkyl of C1~C10, C1
The alkyl of the alkyl of~C8, C1~C6, such as can be methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, Zhong Ding
Base, tert-butyl, amyl, hexyl etc.." naphthenic base of C3~C20 " further can be the naphthenic base of C3~C8, C3~C6
Naphthenic base, such as can be cyclopropane, cyclobutane, pentamethylene, hexamethylene, cycloheptane, cyclooctane etc..
In the inventive solutions, substituent group can be with any position phase of any position and substituted structure
Even, as long as the compound obtained according to the connection type can be prepared by certain method.
In addition, in the present invention, when some group is substituted, can be mono-substituted, two replace, be also possible to
It is polysubstituted.
According to embodiment of the present invention, dihydrobenzo indazole compounds according to the present invention are selected from: A-1 to A-
72。
According to another aspect of the present invention, the preparation method of dihydrobenzo indazole compounds as described above is provided,
Including dihydrobenzo indazole substituent group corresponding to what is be activated is carried out substitution reaction.
The mode of " the corresponding substituent group being activated ", activation for example can be bromination.
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 A-1
Under nitrogen protection, 1000 milliliters of dry toluene, 15.6 grams of (0.1mol) 1,2- bis- are added in 2000 milliliters of there-necked flasks
Hydrogen benzo [cd] indazole, 77.8 grams of bromo- N of (0.24mol) 4-, N- diphenylaniline, 2.9 grams of (0.005mol) Pd (dba)2It is (double
(bis- Ya Benzyl benzylacetone) palladium), the toluene solution (mass concentration 10%) of 10.1 grams of (0.005mol) tri-tert-butylphosphines, 24.96
Gram (0.26mol) sodium tert-butoxide, is slowly heated to flow back, and reacts 8 hours, is slowly dropped to room temperature, aqueous ammonium chloride solution is added to wash,
Liquid separation.Organic layer is washed to neutrality, after magnesium sulfate is dry, silica gel column chromatography separation, and petroleum ether: ethyl acetate: methylene chloride=
5:2:1 (volume ratio) elution, eluent are concentrated to dryness, and obtain 45.0 grams of product shown in formula A-1, yield 70%.
Mass Spectrometer Method has been carried out to product shown in obtained formula A-1, has obtained the m/e:642 of product.
Nuclear-magnetism detection is carried out to product shown in obtained formula A-1, obtained nuclear-magnetism parsing data are as follows:
1HNMR (500MHz, CDCl3): δ 8.00 (m, 2H), δ 8.75 (m, 4H), δ 7.35 (m, 2H), δ 7.25 (m, 15H), δ
7.10 (m, 13H).
The synthesis of compound A-2
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-2.
Compound A-2 is obtained, Mass Spectrometer Method, product m/e:670 are carried out.
The synthesis of compound A-5
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-5.
Compound A-5 is obtained, Mass Spectrometer Method, product m/e:794 are carried out.
The synthesis of compound A-6
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-6.
Compound A-6 is obtained, Mass Spectrometer Method, product m/e:874 are carried out.
The synthesis of compound A-7
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-7.
Compound A-7 is obtained, Mass Spectrometer Method, product m/e:794 are carried out
The synthesis of compound A-8
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-8.
Compound A-8 is obtained, Mass Spectrometer Method, product m/e:794 are carried out
The synthesis of compound A-9
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-9.
Compound A-9 is obtained, Mass Spectrometer Method, product m/e:1122 are carried out.
The synthesis of compound A-10
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-10.
Compound A-10 is obtained, Mass Spectrometer Method, product m/e:1118 are carried out.
The synthesis of compound A-11
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-11.
Compound A-11 is obtained, Mass Spectrometer Method, product m/e:946 are carried out.
The synthesis of compound A-12
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-12.
Compound A-12 is obtained, Mass Spectrometer Method, product m/e:1026 are carried out.
The synthesis of compound A-13
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-13.
Compound A-13 is obtained, Mass Spectrometer Method, product m/e:1275 are carried out.
The synthesis of compound A-14
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-14.
Compound A-14 is obtained, Mass Spectrometer Method, product m/e:1271 are carried out.
The synthesis of compound A-17
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-17.
Compound A-17 is obtained, Mass Spectrometer Method, product m/e:1026 are carried out.
The synthesis of compound A-20
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-20.
Compound A-20 is obtained, Mass Spectrometer Method, product m/e:1351 are carried out.
The synthesis of compound A-24
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-24.
Compound A-24 is obtained, Mass Spectrometer Method, product m/e:742 are carried out.
The synthesis of compound A-25
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-25.
Compound A-25 is obtained, Mass Spectrometer Method, product m/e:942 are carried out.
The synthesis of compound A-29
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-29.
Compound A-29 is obtained, Mass Spectrometer Method, product m/e:1106. are carried out
The synthesis of compound A-31
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-31.
Compound A-31 is obtained, Mass Spectrometer Method, product m/e:994 are carried out.
The synthesis of compound A-34
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-34.
Compound A-34 is obtained, Mass Spectrometer Method, product m/e:1094 are carried out.
The synthesis of compound A-40
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-40.
Compound A-40 is obtained, Mass Spectrometer Method, product m/e:1074 are carried out.
The synthesis of compound A-42
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-42.
Compound A-42 is obtained, Mass Spectrometer Method, product m/e:974 are carried out.
The synthesis of compound A-44
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-44.
Compound A-44 is obtained, Mass Spectrometer Method, product m/e:1122 are carried out.
The synthesis of compound A-47
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-47.
Compound A-47 is obtained, Mass Spectrometer Method, product m/e:1339 are carried out.
The synthesis of compound A-52
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-52.
Compound A-52 is obtained, Mass Spectrometer Method, product m/e:1146 are carried out.
The synthesis of compound A-55
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-55.
Compound A-55 is obtained, Mass Spectrometer Method, product m/e:1194 are carried out.
The synthesis of compound A-61
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-61.
Compound A-61 is obtained, Mass Spectrometer Method, product m/e:794 are carried out.
The synthesis of compound A-62
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-62.
Compound A-62 is obtained, Mass Spectrometer Method, product m/e:874 are carried out.
The synthesis of compound A-66
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-66.
Compound A-66 is obtained, Mass Spectrometer Method, product m/e:874 are carried out.
The synthesis of compound A-71
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-71.
Compound A-71 is obtained, Mass Spectrometer Method, product m/e:806 are carried out.
The synthesis of compound A-72
The synthesis of synthetic method reference compound A-1, only by the bromo- N of 4- therein, N- diphenylaniline is changed intoObtain corresponding compound A-72.
Compound A-72 is obtained, Mass Spectrometer Method, product m/e:970 are carried out.
For other compounds, also obtained using similar synthetic method.
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, which contains
With good grounds dihydrobenzo indazole compounds of the invention.
According to embodiment of the present invention, the hole mobile material of the organic electroluminescence device includes according to this hair
Bright dihydrobenzo indazole compounds.
According to embodiment of the present invention, the hole-injecting material of the organic electroluminescence device includes according to this hair
Bright dihydrobenzo indazole compounds.
The typical structure of organic electroluminescence device are as follows: substrate/anode/hole injection layer/hole transmission layer (HTL)/has
Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescence device structure can be single-shot light
Layer is also possible to multi-luminescent layer.
Wherein, the substrate in conventional organic electroluminescence device can be used in substrate, such as: glass or plastics.Anode can be with
Using transparent high conductivity material, such as: indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO).
The hole-injecting material (Hole Injection Material, abbreviation HIM) of hole injection layer, it is desirable that there is height
Thermal stability (high Tg), have a lesser potential barrier with anode, can vacuum evaporation form pin-hole free films.Commonly HTM 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 level and lumo energy that transport layer matches, the good and hole to match and electron transport ability are good high
Thermal stability and film forming, and suitable singlet or triplet state energy gap are used to control exciton in luminescent layer, there are also with phase
Good energy transfer between the fluorescent dye or phosphorescent coloring answered.The luminescent material of organic luminous layer is needed by taking dyestuff as an example
Have following characteristics: there is high fluorescence or phosphorescence quantum efficiency；The absorption spectrum of dyestuff and the emission spectrum of main body have
Overlapping, i.e. main body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff；The emission peak of red, green, blue to the greatest extent may be used
Can be narrow, with the excitation purity obtained；Stability is good, is able to carry out vapor deposition etc..
The electron transport material (Electron transport Material, abbreviation ETM) of electron transfer layer requires ETM
There are reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy level and LUMO (Lowest Unoccupied
Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and is preferably provided with
Hole blocking ability；Higher electron transport ability, the film forming and thermal stability having had.ETM is typically electron deficient knot
The aromatic compound of the conjugate planes of structure.Electron transfer layer uses Alq3 (8-hydroxyquinoline aluminium) or TAZ (3- phenyl -4-
(1 '-naphthalene) -5- benzene -1,2,4- triazole) either TPBi (1,3,5- tri- (N- phenyl -2- benzimidazole) benzene) or be derived from this three
Any two kinds of 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 used as to of the invention specific
Description, is not intended as limitation of the present invention.Make below in conjunction with the organic electroluminescence device containing the compound of the present invention
For embodiment, the present invention is described further.
The specific structure of material therefor is seen below in embodiment:
Embodiment
Embodiment 1-18 selects the compound of the present invention as the hole mobile material in organic electroluminescence device, compares
Embodiment 1 selects NPB as the hole mobile material in organic electroluminescence device.
Organic electroluminescence device structure are as follows: ITO/HIL02 (100nm)/HTL (40nm)/EM1 (30nm)/Alq3
(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows:
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Water is improved and is infused with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
Enter the binding ability of 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；
Vacuum evaporation the compounds of this invention and NPB are distinguished on hole injection layer as hole transmission layer, evaporation rate is
0.1nm/s, vapor deposition film thickness are 40nm；
Organic luminous layer of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 30nm；
Electron transfer layer of the vacuum evaporation Alq3 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 Al of LiF, 150nm of vacuum evaporation 0.5nm are as electron injecting layer and cathode on the electron transport layer.
Organic electroluminescence device performance is shown in Table 1.
Table 1
It can see by upper table, organic electroluminescence can be improved using the compound of the present invention as hole transmission layer
The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
Embodiment 19-36 selects the compound of the present invention as the hole-injecting material in organic electroluminescence device, than
Select HIL02 as the hole-injecting material in organic electroluminescence device compared with embodiment 2.
Organic electroluminescence device structure are as follows: ITO/HIL (100nm)/NPB (40nm)/EM1 (30nm)/Alq3 (20nm)/
LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows:
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Water is improved and is infused with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
Enter the binding ability of layer；
Above-mentioned glass substrate is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa distinguishes vacuum on anode
HIL02 and the compounds of this invention is deposited as hole injection layer, evaporation rate 0.1nm/s, vapor deposition film thickness is 100nm；
Vacuum evaporation NPB is distinguished on hole injection layer as hole transmission layer, evaporation rate 0.1nm/s, evaporation film
Thickness is 40nm；
Organic luminous layer of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 30nm；
Electron transfer layer of the vacuum evaporation Alq3 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 Al of LiF, 150nm of vacuum evaporation 0.5nm are as electron injecting layer and cathode on the electron transport layer.
Organic electroluminescence device performance is shown in Table 2.
Table 2
It can see by upper table, organic electroluminescence can be improved using the compound of the present invention as hole injection layer
The luminous efficiency of part reduces the driving voltage of organic electroluminescence device.
The above, above embodiments are only described in detail to the technical solution to the application, but the above implementation
The method that the explanation of example is merely used to help understand the embodiment of the present invention, should not be construed as the limitation to the embodiment of the present invention.This
Any changes or substitutions that can be easily thought of by those skilled in the art, should all cover the embodiment of the present invention protection scope it
It is interior.
Claims (10)
1. a kind of dihydrobenzo indazole compounds, which is characterized in that shown in the compound such as formula (A):
Wherein, Ar1To Ar6Be each independently selected from substituted or unsubstituted C6~C60 is free of heteroatomic aryl.
2. dihydrobenzo indazole compounds according to claim 1, which is characterized in that being free of for the C6~C60 is miscellaneous
The aryl of atom is selected from phenyl, naphthalene, anthryl, phenanthryl, cyclopentaphenanthreneyl, two fluorenyl of spiral shell, pyrenyl, triphenylene, fluoranthene base, indenes
And fluorenyl, xenyl, terphenyl, fluorenyl, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl or benzo anthryl.
3. dihydrobenzo indazole compounds according to claim 1, which is characterized in that Ar1And Ar2At least one of
Heteroatomic aryl is free of for substituted C6~C60, substituent group is each independently selected from: the alkyl of C1~C20, C3~C20
Naphthenic base and at least one of phenyl.
4. dihydrobenzo indazole compounds according to claim 1, which is characterized in that Ar3To Ar6At least one of
Heteroatomic aryl is free of for substituted C6~C60, substituent group is each independently selected from: the alkyl of C1~C20, C3~C20
Naphthenic base, phenyl, naphthalene, anthryl, phenanthryl, cyclopentaphenanthreneyl, Spirofluorene-based, pyrenyl, triphenylene, fluoranthene base, indeno fluorenyl,
At least one of xenyl, fluorenyl, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl and benzo anthryl.
5. dihydrobenzo indazole compounds according to claim 1, which is characterized in that the compound meets following three
At least one of a condition: (a) Ar1And Ar2It is identical, (b) Ar3And Ar6It is identical, (c) Ar4And Ar5It is identical.
6. dihydrobenzo indazole compounds according to claim 1, which is characterized in that the compound is selected from:
7. a kind of organic electroluminescence device, which is characterized in that it is any that the organic electroluminescence device contains claim 1-6
The dihydrobenzo indazole compounds.
8. organic electroluminescence device according to claim 6, which is characterized in that the sky of the organic electroluminescence device
Hole transport materials include any dihydrobenzo indazole compounds of claim 1-6.
9. organic electroluminescence device according to claim 6, which is characterized in that the sky of the organic electroluminescence device
Hole injection material includes any dihydrobenzo indazole compounds of claim 1-6.
10. a kind of display device, which is characterized in that including the organic electroluminescence device as described in claim 8-9 is any.
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| CN112687797A (en) * | 2020-11-12 | 2021-04-20 | 烟台海森大数据有限公司 | Organic electroluminescent device and display device comprising same |
| CN114716329A (en) * | 2022-04-01 | 2022-07-08 | 上海钥熠电子科技有限公司 | Organic compound and organic photoelectric device |
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Application publication date: 20190507 |