CN108821984A - Dihydroanthracene compound, organic electroluminescence device and display device - Google Patents
Dihydroanthracene compound, organic electroluminescence device and display device Download PDFInfo
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- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract
The present invention relates to field of display technology, 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
Technical field
The present invention relates to field of display technology, more particularly to a kind of dihydroanthracene compound, organic electroluminescence 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 following advantages 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 functional 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 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 driving voltage with higher and lower luminous efficiency.
Summary of the invention
The present invention provides a kind of dihydroanthracene compound, the organic electroluminescence device comprising the compound and there is this
The display device of organic electroluminescence device, to solve the high driving voltage of organic electroluminescence device in the prior art and low
The problem of luminous efficiency.
According to an aspect of the present invention, a kind of dihydroanthracene compound is provided, shown in the compound such as formula (I)：
Wherein Ar1,Ar2,Ar3The aromatic hydrocarbon being made of carbon and hydrogen for being separately 6~30 selected from total carbon atom number
Base；And Ar1, Ar2, Ar3It can be by the aliphatic alkyl of carbon atoms 1-30, the aliphatic alkoxy of carbon atoms 1-30, carbon
Replaced the aromatic radical of atom 6-20 being made of carbon and hydrogen, this substitution can be monosubstituted, be also possible to polysubstituted.
Further, wherein Ar2, Ar3It is selected from：B-1：
Wherein, Ar7、Ar8、Ar9The aromatic hydrocarbon being made of carbon and hydrogen for being separately 6~30 selected from total carbon atom number
Base；Wherein * indicates the position that B-1 is connected with N atom in compound shown in formula (I).
Further, the aryl radical being made of carbon and hydrogen that total carbon atom number is 6~30 is selected from：Phenyl, xenyl, three
Xenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzene
And fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
Optionally, dihydroanthracene compound according to the present invention is selected from：
It should be noted that the connection type of adjacent group is unique, such as in P- in specific structure listed above
In 1, the four phenyl ring contraposition connected on dihydro anthracene nucleus is replaced by hexichol amido respectively, in fact, being connected on dihydro anthracene nucleus
Phenyl ring meta position by hexichol amido replace and dihydro anthracene nucleus on the ortho position of phenyl ring that is connected replaced by hexichol amido and to be formed
Compound, shown in following (a), (b)：
It can achieve effect of the invention, belong to the content of the invention to be disclosed and be protected.Such the position of substitution
Change, there is no the overall structures for changing the compounds of this invention, without influence on the application technology effect of the compounds of this invention.
Therefore, in the logical formula (I) of the present invention
In, Ar1, Ar2, Ar3Connection type or Ar between representative structure1, Ar2, Ar3Representative inside configuration
The change of connection type between different or identical group, within the scope of belonging to disclosure of the invention and protecting.
According to another aspect of the present invention, a kind of organic electroluminescence device, the organic electroluminescence device are provided
Include dihydroanthracene compound according to the present invention.
Optionally, the material of the hole injection layer of the organic electroluminescence device or hole transmission layer is according to the present invention
Dihydroanthracene compound.
According to another aspect of the present invention, a kind of display device is provided, which includes according to the present invention having
Organic electroluminescence devices.
Meanwhile the present invention also provides a kind of electronic equipment, which contains electronic display screen.
Further, above-mentioned electronic equipment is selected from：Mobile phone, computer, tablet computer, wrist-watch, VR display, digital camera,
Bracelet, counter, electronic watch.
Beneficial effects of the present invention are as follows：
Compound provided by the invention is used for the hole transmission layer or hole injection layer of organic electroluminescence device, is improved
The luminous efficiency of organic electroluminescence device, the driving voltage for reducing organic electroluminescence device.
Specific 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.
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 compound P-1
In 500 milliliters of there-necked flask, under nitrogen protection, 200 milliliters of dry dimethyl sulfoxides 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- dihydroanthracene, is stirred in 30 DEG C
30 minutes, 19.45 grams of (0.06mol) 4- bromine triphenylamines are added, 60 DEG C is warming up to and reacts 1 hour, then are warming up to 80 DEG C of reactions 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 Decomposition mistake is added
Then the sodium hydride of amount is added 300 milliliters of dilute hydrochloric acid, filtering, obtained solid washing, methanol washs, then with silicagel column point
From using petroleum ether：Ethyl acetate (volume ratio 10：1) it is eluted as eluant, eluent, obtains product 1.8 shown in formula P-1
Gram, yield 15.6%.
To obtained compound P-1, Mass Spectrometer Method, product m/e are carried out：1153.
Nuclear-magnetism detection is carried out to obtained compound P-1, the parsing data of obtained nuclear magnetic spectrogram are as follows：
1HNMR (500MHz, CDCl3)：δ 7.24 (m, 16H), δ 7.20~7.13 (m, 12H), δ 7.09 (m, 16H), δ
6.98 (m, 8H), δ 6.88 (m, 8H), δ 6.69 (m, 4H).
Elemental analysis carried out to obtained compound 1, and measured value % (C, 89.38；H, 5.60；N, 4.88), calculated value
(C,89.55；H,5.59；N,4.86).
The synthesis of other parts compound of the present invention
Synthetic method only changes 4- bromine triphenylamine therein into corresponding bromine as needed referring to the synthetic method of P-1
For aromatic amine compounds, Mass Spectrometer Method, raw material used in synthesis process and product mass spectrum have been carried out to obtained compound
Testing result see the table below：
According to another aspect of the present invention, a kind of organic electroluminescence device is provided, the organic electroluminescence device
The material of hole transmission layer or hole injection layer is according to the compound of the present invention.
The typical structure of organic electroluminescence device is：Substrate/anode/hole injection layer/hole transmission layer (HTL)/has
Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/cathode.Organic electroluminescence device structure can be single-shot light
Layer 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 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 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：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, 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 1
Hole mobile material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison
Electroluminescence device, hole mobile material select NPB.
Organic electroluminescence device structure is：ITO/HIL02(100nm)/HTL(40nm)/EM1(30nm)/ETL
(20nm)/LiF(0.5nm)/Al(150nm)。
Glass substrate is selected in organic electroluminescence device production in the present embodiment, ITO makees anode material, and HIL02 makees
Hole injection layer, EM1 make the material of main part of organic luminous layer, and TAZ makees electron injection as electron transport layer materials, LiF/Al
Layer/cathode material.
Organic electroluminescence device preparation process in the present embodiment is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Water is improved and is passed with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
The binding ability of defeated layer.
Above-mentioned glass substrate is placed in vacuum chamber, vacuum evaporation HIL02 is as hole injection layer, vapor deposition speed on anode
Rate 0.1nm/s, vapor deposition film thickness are 100nm.
The vacuum evaporation hole transmission layer on hole injection layer, evaporation rate 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 TAZ as organic electroluminescence device on organic luminous layer；Speed is deposited in it
Rate is 0.1nm/s, and vapor deposition total film thickness is 20nm.
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL)；
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 1：
Table 1
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 2
Hole-injecting material in using the compound of the present invention as organic electroluminescence device, Organic Electricity as a comparison
Electroluminescence device, hole-injecting material select HIL02.
Organic electroluminescence device structure is：ITO/HIL(100nm)/NPB(40nm)/EM1(30nm)/ETL(20nm)/
LiF(0.5nm)/Al(150nm)。
Glass substrate is selected in organic electroluminescence device production in the present embodiment, ITO makees anode material, and NPB makees empty
Cave transport layer, EM1 make the material of main part of organic luminous layer, TAZ as electron transport layer materials, LiF/Al make electron injecting layer/
Cathode material.
Organic electroluminescence device preparation process in the present embodiment is as follows：
The glass substrate for being coated with transparent conductive layer (as anode) is ultrasonically treated in cleaning agent, then
It rinses in deionized water, then the ultrasonic oil removing in acetone and alcohol mixed solvent, then is baked under clean environment and removes completely
Water is improved and is passed with hole to improve the property on surface with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface
The binding ability of defeated layer.
Above-mentioned glass substrate is placed in vacuum chamber, the vacuum evaporation hole injection layer on anode, evaporation rate 0.1nm/
S, vapor deposition film thickness are 100nm.
Vacuum evaporation NPB is as hole transmission layer on hole injection layer, and evaporation rate 0.1nm/s, film thickness, which is deposited, is
40nm。
Organic luminous 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 TAZ as organic electroluminescence device on organic luminous layer；Speed is deposited in it
Rate is 0.1nm/s, and vapor deposition total film thickness is 20nm.
The LiF of vacuum evaporation 0.5nm is as electron injecting layer on electron transfer layer (ETL)；
The aluminium (Al) of vacuum evaporation 150nm is used as cathode on electron injecting layer.
Organic electroluminescence device performance is shown in Table 2：
Table 2
| Hole-injecting material | It is required that brightness cd/m2 | Driving voltage V | Current efficiency cd/A |
| HIL02 | 1000 | 5.83 | 1.39 |
| Compound P-26 | 1000 | 5.63 | 1.5 |
| Compound P-28 | 1000 | 4.3 | 1.52 |
| Compound P-29 | 1000 | 4.14 | 1.58 |
| Compound P-32 | 1000 | 5.15 | 1.5 |
| Compound P-34 | 1000 | 4.9 | 1.57 |
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.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
Mind 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 (9)
1. a kind of dihydroanthracene compound, as shown in formula (I)：
Wherein Ar1,Ar2,Ar3The aryl radical being made of carbon and hydrogen for being separately 6~30 selected from total carbon atom number；
The Ar1, Ar2, Ar3Can by the aliphatic alkyl of carbon atoms 1-30, carbon atoms 1-30 aliphatic alkoxy,
Replaced the aromatic radical of carbon atom 6-20 being made of carbon and hydrogen.
2. dihydroanthracene compound according to claim 1,
Wherein Ar2, Ar3It is selected from：B-1：
Wherein, Ar7、Ar8、Ar9The aryl radical being made of carbon and hydrogen for being separately 6~30 selected from total carbon atom number；
Wherein * indicates the position that B-1 is connected with N atom in compound shown in formula (I).
3. dihydroanthracene compound according to claim 1, the fragrance being made of carbon and hydrogen that total carbon atom number is 6~30
Alkyl is selected from：Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indenofluorene
Base, cyclopentaphenanthreneyl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
4. dihydroanthracene compound according to claim 2, wherein total carbon atom number is 6~30 to be made of carbon and hydrogen
Aryl radical is selected from：
Phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, triphenylene, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, ring
Penta and phenanthryl, Spirofluorene-based, benzo fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
Dihydroanthracene compound below 5.：
6. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes claim 1-5 any
The dihydroanthracene compound.
7. organic electroluminescence device according to claim 6, which is characterized in that the hole of the organic electroluminescence device
The material of transport layer or hole injection layer is any dihydroanthracene compound of claim 1-5.
8. a kind of display device, which is characterized in that including the organic electroluminescence device as described in claim 6~7 is any.
9. a kind of electronic equipment, comprising display device described in claim 8, the electronic equipment is selected from mobile phone, computer, plate electricity
Brain, wrist-watch, VR display, digital camera, bracelet, counter, electronic watch.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810365945.1A CN108821984A (en) | 2018-04-23 | 2018-04-23 | Dihydroanthracene compound, organic electroluminescence device and display device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810365945.1A CN108821984A (en) | 2018-04-23 | 2018-04-23 | Dihydroanthracene compound, organic electroluminescence device and display device |
Publications (1)
| Publication Number | Publication Date |
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| CN108821984A true CN108821984A (en) | 2018-11-16 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109776334A (en) * | 2018-12-29 | 2019-05-21 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compounds and its preparation method and device |
| WO2019220276A1 (en) * | 2018-05-17 | 2019-11-21 | 株式会社半導体エネルギー研究所 | Organic compound, light-emitting element, light-emitting device, electronic apparatus, illumination device, and electronic device |
| CN111574383A (en) * | 2020-05-26 | 2020-08-25 | 烟台显华化工科技有限公司 | Organic light-emitting material and organic electroluminescent device |
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| CN103503188A (en) * | 2011-05-05 | 2014-01-08 | 默克专利有限公司 | Compounds for electronic devices |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103503188A (en) * | 2011-05-05 | 2014-01-08 | 默克专利有限公司 | Compounds for electronic devices |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019220276A1 (en) * | 2018-05-17 | 2019-11-21 | 株式会社半導体エネルギー研究所 | Organic compound, light-emitting element, light-emitting device, electronic apparatus, illumination device, and electronic device |
| JPWO2019220276A1 (en) * | 2018-05-17 | 2021-07-01 | 株式会社半導体エネルギー研究所 | Organic compounds, light emitting elements, light emitting devices, electronic devices, lighting devices and electronic devices |
| JP7345456B2 (en) | 2018-05-17 | 2023-09-15 | 株式会社半導体エネルギー研究所 | Electronic devices and organic compounds |
| US11964928B2 (en) | 2018-05-17 | 2024-04-23 | Semiconductor Energy Laboratory Co., Ltd. | Organic compound, light-emitting device, light-emitting apparatus, electronic equipment, lighting device, and electronic device |
| CN109776334A (en) * | 2018-12-29 | 2019-05-21 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compounds and its preparation method and device |
| CN109776334B (en) * | 2018-12-29 | 2021-12-10 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compounds, method of manufacturing the same and devices using the same |
| CN111574383A (en) * | 2020-05-26 | 2020-08-25 | 烟台显华化工科技有限公司 | Organic light-emitting material and organic electroluminescent device |
| CN111574383B (en) * | 2020-05-26 | 2023-06-20 | 烟台显华化工科技有限公司 | Organic luminescent material and organic electroluminescent device |
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Application publication date: 20181116 |