CN109608385A - A kind of organic material and its preparation and application - Google Patents
A kind of organic material and its preparation and application Download PDFInfo
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Abstract
The present invention relates to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical fields, and in particular to a kind of organic material and its preparation and application, the organic material have the structure as shown in general formula I:
Description
Technical field
The present invention relates to a kind of new organic materials, and its application in organic electroluminescence device, belong to Organic Electricity
Photoluminescence field of display technology.
Background technique
Application of organic electroluminescent (OLED) material in the fields such as information display material, organic optoelectronic material has
Great researching value and fine application prospect.With the development of multimedia information technology, to flat-panel display device performance
It is required that higher and higher.Current main display technology has plasma display apparatus, field emission display and organic electroluminescent
Display device (OLED).Wherein, OLED has itself luminous, low-voltage direct-current driving, all solidstate, the wide, various colors in visual angle etc.
Series of advantages, compared with liquid crystal display device, OLED does not need backlight, and visual angle is wider, low in energy consumption, and response speed is liquid
1000 times of crystal display device, therefore, OLED have broader practice prospect.
For the organic hole transport material reported at present since molecular weight is generally smaller, the glass transition temperature of material is lower,
During materials'use, charging and discharging, material are easy crystallization repeatedly, and the homogeneity of film is destroyed, to influence materials'use
Service life.Therefore, the organic hole transport material of stability and high efficiency is developed, to reduce driving voltage, device light emitting efficiency is improved, prolongs
Long device lifetime has critically important practical application value.
Summary of the invention
The invention proposes a kind of novel organic materials, have the structure as shown in general formula I:
In general formula I, Ar is selected from:
One of；
M is selected from 1 to 4 integer,It indicates to replace position.
Material of the present invention can prepare low voltage drive, long-life and efficient OLED element.
Preferably, Ar is selected from:
One of；
M is 1 or 2.
Preferably, the organic material are as follows:
Above-mentioned organic material is due to containing methyl on phenyl ring, so as to increase intermolecular distance, prevent compound it
Between association, reduce the probability of molecule piled up, make the organic material have preferable dissolubility and suitable mobility,
The crosstalk between pixel will not occur, reduce the HOMO value of material molecule, more conducively hole is injected.Thermal stability is good, when vapor deposition
It is less likely to occur to crystallize, OLED yield rate can be effectively improved by being applied in OLED device, reduced driving voltage, improved luminous
Efficiency increases the service life.
The present invention also provides the preparation methods of this organic material, include the following steps:
A) using compound 1-1 as starting material, withCoupling reaction occurs, obtains compound 1-2；
B) coupling reaction occurs for the compound 1-2 and Br-Ar-Br, obtains compound 1；
Wherein, the reference of Ar and m is identical as specification reference above-mentioned.
Known common approach can be used to realize in above-mentioned step those skilled in the art, such as selects suitable catalysis
Agent, solvent determine suitable reaction temperature, and time etc., the present invention is not particularly limited this.
Preferably, the preparation method of the compound of the invention includes the following steps:
A) using compound 1-1 as starting material, using toluene as solvent, with three (hexichol benzylacetone) two palladiums and tri-tert
Phosphine is catalyst, and sodium tert-butoxide is alkali, nitrogen protection, 100-110 DEG C of temperature control, compound 1-1 withCoupling reaction occurs,
Obtain compound I-2；
B) using dimethylbenzene as solvent, using three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine as catalyst, sodium tert-butoxide
For alkali, nitrogen protection, 110-120 DEG C of temperature control, coupling reaction occurs for compound 1-2 and Br-Ar-Br, obtains compound 1；
Wherein, the reference of Ar and m is identical as specification reference above-mentioned.
Above-mentioned dibromo condensed-nuclei aromatics, sodium tert-butoxide and three (hexichol benzylacetone) two palladiums etc. can pass through open business way
Method known per se synthesizes to obtain in diameter or document.
Another object of the present invention is protection organic material of the present invention in preparing organic electroluminescence device
Application.
Preferably, material of the organic material of the present invention as the hole transmission layer prepared in organic electroluminescence device
Material.
Another object of the present invention is to protect a kind of organic electroluminescence device, the material of the device hole-transporting layer
Material is organic material of the present invention.
Preferably, the luminescent device successively include the transparent substrate being stacked, it is anode layer, hole transmission layer, organic
Luminescent layer, electron transfer layer, electron injecting layer and cathode layer.
Preferably, the material for constituting the transparent substrate is glass substrate or flexible substrate；
Preferably, the substrate in conventional organic luminescence device can be used in the flexible substrate, such as glass or plastics.
The material for preferably constituting the anode layer is inorganic material；
It is further preferred that the inorganic material be specially tin indium oxide (ITO), zinc oxide, zinc tin oxide, gold, silver or
At least one of copper, preferably tin indium oxide (ITO)；
As a preferred option, glass substrate is preferably selected in element manufacturing of the invention, ITO makees anode material.
Preferably, the material of the organic luminous layer is prepared are as follows:
One of；
Preferably, the material of the electron transfer layer is prepared are as follows:
One of；
Preferably, the material for preparing the electron injecting layer is LiF, Li2O, MgO or Al2O3One of, preferably LiF.
Preferably, the material for constituting the cathode is selected from one of lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin；
Further preferred aluminium.
As a preferred solution, the luminescent device of the invention,
The hole transmission layer with a thickness of 10-50nm, preferably 30nm；
The organic luminous layer with a thickness of 10-100nm, preferably 50nm；
The electron transfer layer with a thickness of 10-30nm, preferably 15nm；
The electron injecting layer with a thickness of 5-30nm, preferably 30nm；
The cathode with a thickness of 50-110nm, preferably 60nm.
The invention has the following beneficial effects:
Organic material provided by the invention is centered on fused ring compound, using methylic (aniline is end group), by
The active position of polycyclc aromatic compound introduces the substituent group with hole transport performance, obtains a kind of with hole biography
The novel OLED material of defeated performance.Such material has high hole mobility, preferable thin film stability, suitable molecule energy
Grade and higher glass transition temperature, can also improve the luminous efficiency of carrier transport efficiency and device.It can be applied
In field of organic electroluminescence, used as hole mobile material.
Specific embodiment
Tri-tert-butylphosphine used in the present invention, sodium tert-butoxide, three (hexichol benzylacetone) two palladiums, dibromo polycyclic aromatic hydrocarbon etc.
Industrial chemicals can conveniently be bought in chemical products market at home.
Embodiment 1
Synthetic route is as follows:
1) synthesis of compound 1-2
1000 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 46.1g (0.48mol), 2- after argon gas displacement
Aniline 27.94g (purity 99%, 0.3mol), 67.25g the bromo- 1- methyl -9- phenyl -9H- carbazole of 6- (purity 99%,
0.2mol) and toluene 400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) are sequentially added after argon gas displacement again
Two palladiums.After adding, opens agitating and heating and be warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.It is cooled to after 30 DEG C through silicagel column
Filtrate is filtered to obtain, filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, anhydrous slufuric acid is used in liquid separation
Sodium is dried, and filters, and rotates filtrate, obtains 62.72g yellow product, purity 99%, yield 90%.
2) synthesis of compound 1
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 18.1g (0.188mol), 9 after argon gas displacement,
10- dibromoanthracene 26.4g (purity 99%, 0.0785mol) and dimethylbenzene 100ml.1.6ml tri- is sequentially added after argon gas displacement again
Tert-butyl phosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise by 70.73g
The bis- phenyl -9H- carbazole -3- amine of 8- methyl-N, 9- (purity 99%, 0.203mol) and 100ml dimethylbenzene composition solution, control
Warm 110-120 DEG C.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake is boiled repeatedly with DMF
Several times, 58.12g yellow product, purity 99%, yield 85% are obtained.
Product MS (m/e): 871.08；Elemental analysis (C64H46N4): theoretical value C:88.25%, H:5.32%, N:
6.43%；Measured value C:88.54%, H:5.34%, N:6.42%.
Embodiment 2
Synthetic route is as follows:
1) synthesis of compound 2-1
1000 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 46.1g (0.48mol), 2- after argon gas displacement
Aniline 27.94g (purity 99%, 0.3mol), 67.25g the bromo- 1- methyl -9- phenyl -9H- carbazole of 6- (purity 99%,
0.2mol) and dimethylbenzene 400ml.3ml tri-tert-butylphosphine and (the hexichol benzyl third of 0.46g tri- are sequentially added after argon gas displacement again
Ketone) two palladiums.After adding, opens agitating and heating and be warming up to 110 DEG C, 110-120 DEG C of temperature control is reacted 5 hours.It is cooled to after 30 DEG C through silicon
Rubber column gel column filters to obtain filtrate, rotates filtrate, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, liquid separation, use is anhydrous
Sodium sulphate is dried, and filters, and rotates filtrate, obtains 62.02g yellow product, purity 99%, yield 89%.
2) synthesis of compound 2
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 18.1g (0.188mol), 9 after argon gas displacement,
The bromo- 2- methyl anthracene 27.5g (purity 99%, 0.0785mol) of 10- bis- and dimethylbenzene 100ml.It is sequentially added after argon gas displacement again
1.6ml tri-tert-butylphosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise
It is made of 8- methyl-N, the 9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene of 70.73g
Solution, 110-120 DEG C of temperature control.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake is used
DMF boils several times repeatedly, obtains 56.28g yellow product, purity 99%, yield 81%.
Product MS (m/e): 885.10；Elemental analysis (C65H48N4): theoretical value C:88.20%, H:5.47%；N:
6.33%；Measured value C:88.19%, H:5.49%, N:6.32%.
Embodiment 3
Synthetic route is as follows:
1) synthesis of compound 3-1
1000 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 46.1g (0.48mol), 2- after argon gas displacement
Aniline 27.94g (purity 99%, 0.3mol), 67.25g the bromo- 1- methyl -9- phenyl -9H- carbazole of 6- (purity 99%,
0.2mol) and toluene 400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) are sequentially added after argon gas displacement again
Two palladiums.After adding, opens agitating and heating and be warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.It is cooled to after 30 DEG C through silicagel column
Filtrate is filtered to obtain, filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, anhydrous slufuric acid is used in liquid separation
Sodium is dried, and filters, and rotates filtrate, obtains 62.72g yellow product, purity 99%, yield 90%.
2) synthesis of compound 3
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 18.1g (0.188mol), 6 after argon gas displacement,
12- dibromo bends 24g (purity 99%, 0.0785mol) and dimethylbenzene 100ml.Tri- uncle of 1.6ml is sequentially added after argon gas displacement again
Butyl phosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise by 70.73g's
The solution of 8- methyl-N, 9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene composition, temperature control
110-120℃.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake is boiled several repeatedly with DMF
It is secondary, obtain 62.19g yellow product, purity 99%, yield 86%.
Product MS (m/e): 921.14；Elemental analysis (C68H48N4): theoretical value C:88.67%, H:5.25%, N:
6.08%；Measured value C:88.65%, H:5.28%, N:6.07%.
Embodiment 4
Synthetic route is as follows:
1) synthesis of compound 4-1
1000 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 46.1g (0.48mol), 2- after argon gas displacement
Aniline 27.94g (purity 99%, 0.3mol), 67.25g the bromo- 1- methyl -9- phenyl -9H- carbazole of 6- (purity 99%,
0.2mol) and toluene 400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) are sequentially added after argon gas displacement again
Two palladiums.After adding, opens agitating and heating and be warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.It is cooled to after 30 DEG C through silicagel column
Filtrate is filtered to obtain, filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, anhydrous slufuric acid is used in liquid separation
Sodium is dried, and filters, and rotates filtrate, obtains 62.72g yellow product, purity 99%, yield 90%.
2) synthesis of compound 4
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 18.1g (0.188mol), 3 after argon gas displacement,
Bromo- [1,10] the Phen 26.53g (purity 99%, 0.0785mol) of 8- bis- and dimethylbenzene 100ml.Again argon gas displacement after according to
Secondary addition 1.6ml tri-tert-butylphosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start
It is added dropwise in 8- methyl-N, the 9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml diformazan by 70.73g
The solution of benzene composition, 110-120 DEG C of temperature control.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filters, filter
Cake is boiled several times repeatedly with DMF, obtains 58.25g yellow product, purity 99%, yield 85%.
Product MS (m/e): 873.05；Elemental analysis (C62H44N6): theoretical value C:85.29%, H:5.08%, N:
9.63%；Measured value C:85.28%, H:5.09%, N:9.63%.
Embodiment 5
Synthetic route is as follows:
1) synthesis of compound 5-1
1000 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 46.1g (0.48mol), 2- after argon gas displacement
Aniline 27.94g (purity 99%, 0.3mol), 67.25g the bromo- 1- methyl -9- phenyl -9H- carbazole of 6- (purity 99%,
0.2mol) and toluene 400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) are sequentially added after argon gas displacement again
Two palladiums.After adding, opens agitating and heating and be warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.It is cooled to after 30 DEG C through silicagel column
Filtrate is filtered to obtain, filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, anhydrous slufuric acid is used in liquid separation
Sodium is dried, and filters, and rotates filtrate, obtains 62.72g yellow product, purity 99%, yield 90%.
2) synthesis of compound 5
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 18.1g (0.188mol), 2 after argon gas displacement,
Bis- bromo- pyrene 28.26g (purity 99%, 0.0785mol) and dimethylbenzene 100ml of 7-.1.6ml is sequentially added after argon gas displacement again
Tri-tert-butylphosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start be added dropwise by
8- methyl-N, 9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml the dimethylbenzene composition of 70.73g
Solution, 110-120 DEG C of temperature control.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake DMF
It boils repeatedly several times, obtains 59.72g yellow product, purity 99%, yield 85%.
Product MS (m/e): 895.10；Elemental analysis (C66H48N4): theoretical value C:88.56%, H:5.18%, N:
6.26%；Measured value C:88.55%, H:5.19%, N:6.26%.
Embodiment 6
Synthetic route is as follows:
1) synthesis of compound 6-1
1000 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 46.1g (0.48mol), 2- after argon gas displacement
Aniline 27.94g (purity 99%, 0.3mol), 67.25g the bromo- 1- methyl -9- phenyl -9H- carbazole of 6- (purity 99%,
0.2mol) and toluene 400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) are sequentially added after argon gas displacement again
Two palladiums.After adding, opens agitating and heating and be warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.It is cooled to after 30 DEG C through silicagel column
Filtrate is filtered to obtain, filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, anhydrous slufuric acid is used in liquid separation
Sodium is dried, and filters, and rotates filtrate, obtains 62.72g yellow product, purity 99%, yield 90%.
2) synthesis of compound 6
500 milliliters of there-necked flasks match magnetic agitation, sequentially add sodium tert-butoxide 18.1g (0.188mol), 2 after argon gas displacement,
7 '-two bromo- two fluorenes 37.22g of spiral shell (purity 99%, 0.0785mol) and dimethylbenzene 100ml.It is sequentially added after argon gas displacement again
1.6ml tri-tert-butylphosphine and 0.23g tri- (hexichol benzylacetone) two palladiums.After adding, it is heated to 110 DEG C.Start to be added dropwise
It is made of 8- methyl-N, the 9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene of 70.73g
Solution, 110-120 DEG C of temperature control.50 DEG C are cooled to, the hydrolysis of 100m deionized water is added, stirs 10 minutes, filtering, filter cake is used
DMF boils several times repeatedly, obtains 59.72g yellow product, purity 99%, yield 85%.
Product MS (m/e): 1009.24；Elemental analysis (C75H52N4): theoretical value C:89.26%, H:5.19%, N:
5.55%；Measured value C:89.25%, H:5.20%, N:5.55%.
Technical solution according to embodiment 1- embodiment 6, it is only necessary to which the corresponding raw material of simple replacement does not change any essence
Property operation, following compound can be synthesized.
The integer that the m is 1~3.
Embodiment 7 prepares device OLED-1~OLED-4
1) glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rushed in deionized water
It washes, at acetone/ethanol in the mixed solvent ultrasound 30 minutes, is baked to is completely dried under a clean environment, use ultraviolet rays cleaning
Machine irradiates 10 minutes, and with low energy cation beam bombarded surface.
2) the above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-4Pa,
The compound 1 that one layer of preparation gained ownership Formulas I of embodiment 1 is deposited on above-mentioned anode tunic is hole transmission layer, and evaporation rate is
0.2nm/s, vapor deposition film thickness are 30nm；
3) continue to be deposited ADN on the hole transport layer as material of main part, as the organic luminous layer of device, evaporation rate
Film thickness for 0.2nm/s, vapor deposition gained organic luminous layer is 50nm；
4) continue that electron transfer layer of the one layer of compound BCP as device is deposited on organic luminous layer, evaporation rate is
0.2nm/s, vapor deposition film thickness are 15nm；
5) continue that electron injecting layer of the one layer of LiF as device is deposited on electron transfer layer, evaporation rate is
0.2nm/s, vapor deposition film thickness are 30nm；
6) continue that cathode of the one layer of Al as device, evaporation rate 0.2nm/s, vapor deposition is deposited on electron injecting layer
Film thickness is 60nm；OLED device provided by the invention is obtained, OLED-1 is denoted as；
According to upper identical step, by the compound 1 in step 2) replace with embodiment 2 preparation gained compound 2, obtain
To OLED-2 provided by the invention；
According to upper identical step, by the compound 1 in step 2) replace with embodiment 3 preparation gained compound 3, obtain
To OLED-3 provided by the invention；
According to upper identical step, the compound 1 in step 2) is replaced with into NPB, obtains comparative device OLED-4；
The performance test results of obtained device OLED-1 to OLED-4 are as shown in table 1.
The performance test results of table 1, OLED-1 to OLED-4
From the foregoing, it will be observed that the device OLED-1 being prepared into using organic material shown in Formulas I provided by the invention is to OLED-4's
Bright voltage is lower, brightness under the same conditions, the obvious device OLED-4 than NPB as hole mobile material of current efficiency
It is much higher, and the service life of device is obviously prolonged very much.
Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above embodiments, should manage
Solution, under the guidance of present inventive concept, those skilled in the art can carry out various modifications and improve, and appended claims summarise
The scope of the present invention.
Claims (10)
1. a kind of organic material, which is characterized in that have the structure as shown in general formula I:
In general formula I, Ar is selected from:
One of；
M is selected from integer of 1 to 3,It indicates to replace position.
2. organic material according to claim 1, which is characterized in that the Ar is selected from:
One of；
M is 1 or 2.
3. organic material according to claim 1 or 2, which is characterized in that the organic material are as follows:
4. the preparation method of any one of claims 1 to 3 organic material, which comprises the steps of:
A) using compound 1-1 as starting material, withCoupling reaction occurs, obtains compound 1-2；
B) coupling reaction occurs for the compound 1-2 and Br-Ar-Br, obtains compound 1；
Wherein, the reference of Ar and m is the same as described in claim any one of 1-3.
5. the preparation method of organic material according to claim 4, which comprises the steps of:
A) using compound 1-1 as starting material, using toluene as solvent, it is with three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine
Catalyst, sodium tert-butoxide are alkali, nitrogen protection, 100-110 DEG C of temperature control, compound 1-1 withCoupling reaction occurs, obtains
Compound I-2；
B) using dimethylbenzene as solvent, using three (hexichol benzylacetone) two palladiums and tri-tert-butylphosphine as catalyst, sodium tert-butoxide is alkali,
Nitrogen protection, 110-120 DEG C of temperature control, coupling reaction occurs for compound 1-2 and Br-Ar-Br, obtains compound 1；
Wherein, the reference of Ar and m is the same as described in claim any one of 1-3.
6. the described in any item organic materials of claims 1 to 3 are preparing the application in organic electroluminescence device；Preferably,
The organic material is preparing the application in the hole transmission layer in the organic electroluminescence device.
7. a kind of organic electroluminescence device, which is characterized in that the material of the device hole-transporting layer be claim 1~
3 described in any item organic materials.
8. luminescent device according to claim 7, which is characterized in that the luminescent device successively include be stacked it is saturating
Bright substrate, anode layer, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and cathode layer.
9. luminescent device according to claim 8, which is characterized in that
Prepare the material of the anode layer at least one of tin indium oxide, zinc oxide, zinc tin oxide, gold, silver or copper, preferably
Tin indium oxide；
And/or prepare the material of the organic luminous layer are as follows:
One of；
And/or prepare the material of the electron transfer layer are as follows:
One of；
And/or preparing the material of the electron injecting layer is LiF, Li2O, MgO or Al2O3One of, preferably LiF；
And/or prepare the material of the cathode layer for one of lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, gold or silver, preferably
Aluminium.
10. luminescent device according to claim 8 or claim 9, which is characterized in that
The hole transmission layer with a thickness of 10-50nm, preferably 30nm；
And/or the organic luminous layer with a thickness of 10-100nm, preferably 50nm；
And/or the electron transfer layer with a thickness of 10-30nm, preferably 15nm；
And/or the electron injecting layer with a thickness of 5-30nm, preferably 30nm；
And/or the cathode with a thickness of 50-110nm, preferably 60nm.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109608386A (en) * | 2018-12-10 | 2019-04-12 | 北京燕化集联光电技术有限公司 | A kind of organic material and its application in the devices |
| CN109608383A (en) * | 2018-12-10 | 2019-04-12 | 北京燕化集联光电技术有限公司 | A kind of electroluminescent organic material and the preparation method and application thereof |
| CN109608384A (en) * | 2018-12-10 | 2019-04-12 | 北京燕化集联光电技术有限公司 | A kind of organic material and preparation method thereof and its application in electroluminescent device |
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|---|---|---|---|---|
| CN1978441A (en) * | 2004-11-29 | 2007-06-13 | 三星Sdi株式会社 | Phenylcarbazole-based compound and organic electroluminescent device employing the same |
| CN108003089A (en) * | 2016-10-27 | 2018-05-08 | 江苏三月光电科技有限公司 | Using anthracene as core compound and organic electroluminescence device and its application |
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2018
- 2018-12-10 CN CN201811506529.5A patent/CN109608385A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1978441A (en) * | 2004-11-29 | 2007-06-13 | 三星Sdi株式会社 | Phenylcarbazole-based compound and organic electroluminescent device employing the same |
| CN108003089A (en) * | 2016-10-27 | 2018-05-08 | 江苏三月光电科技有限公司 | Using anthracene as core compound and organic electroluminescence device and its application |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109608386A (en) * | 2018-12-10 | 2019-04-12 | 北京燕化集联光电技术有限公司 | A kind of organic material and its application in the devices |
| CN109608383A (en) * | 2018-12-10 | 2019-04-12 | 北京燕化集联光电技术有限公司 | A kind of electroluminescent organic material and the preparation method and application thereof |
| CN109608384A (en) * | 2018-12-10 | 2019-04-12 | 北京燕化集联光电技术有限公司 | A kind of organic material and preparation method thereof and its application in electroluminescent device |
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