CN109503460A - A kind of organic material and the preparation method and application thereof - Google Patents
A kind of organic material and the preparation method and application thereof Download PDFInfo
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Abstract
The present invention relates to organic electroluminescent (OLED) field of display technology, in particular to a kind of organic material and preparation method thereof and application in the devices, the organic material structure is as shown in general formula I.The present invention is centered on fused ring compound, using (aniline is end group) containing fluorine atom, by in the active position of polycyclc aromatic compound, the substituent group (N- (2- fluorophenyl) -9- phenyl -9H- carbazole -3- amine) with hole transport performance is introduced, a kind of novel OLED material with hole transport performance is obtained.Such material has high hole mobility, preferable thin film stability and suitable molecular entergy level, can be used in field of organic electroluminescence, use as hole mobile material.
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 purpose of the present invention is to provide can carry out low voltage drive, the long-life and the OLED element of high efficiency,
And it can provide the compound of such OLED element.
Specifically, there is the structure as shown in general formula I present invention firstly provides a kind of novel organic material:
In general formula I, Ar is selected from:
M is the integer of 1-4；
It indicates to replace position.
Preferably, in general formula I:
Ar is selected from:
M is 1 or 2.
As further preferred technical solution, the organic material is selected from one kind of following compound:
Wherein, m is the integer of 1-4.
Above-mentioned organic material, so as to increase intermolecular distance, prevents compound due to containing fluorine atom on phenyl ring
Between association, reduce the probability of molecule piled up.It is less likely to occur to crystallize when vapor deposition, being applied in OLED device can have
Effect improves OLED yield rate, reduces driving voltage, improves luminous efficiency, increase the service life.
Invention also provides the preparation method of above-mentioned organic material, the reaction mechanism mechanism of reaction is as follows:
Include the following steps:
1) using compound 1-1 as starting material, withCoupling reaction occurs, obtains compound 1-2；
2) coupling reaction occurs for compound 1-2 and Br-Ar-Br, obtains compound 1.
Wherein, Ar and m refers specifically to generation ibid restriction about organic material.
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, above-mentioned preparation method includes the following steps:
1) 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 withIt is anti-that coupling occurs
It answers, obtains compound I-2；
2) 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, Ar and m refers specifically to generation ibid restriction about organic material.
Above-mentioned Br-Ar-Br, sodium tert-butoxide and three (hexichol benzylacetone) two palladiums etc. can by public commercial source or
Method known per se synthesizes to obtain in person's document.
Invention further provides application of the above-mentioned organic material in organic electroluminescence device.
Preferably, organic material of the present invention is used as hole transmission layer in organic electroluminescence device.
It include above-mentioned general formula compound in organic function layer the present invention also provides a kind of organic electroluminescence device,
Such compound is used as the hole mobile material in organic function layer.
Preferably, above-mentioned organic electroluminescence device from the bottom to top successively by transparent substrate, anode layer, hole transmission layer,
Organic luminous layer, electron transfer layer, electron injecting layer and cathode layer composition.
The material for constituting the transparent substrate is glass substrate or flexible substrate；
The substrate in conventional organic luminescence device can be used in substrate, such as: glass or plastics.
The material for constituting the anode layer is inorganic material；Wherein, the inorganic material be specially tin indium oxide (ITO),
At least one of zinc oxide, zinc tin oxide, gold, silver or copper, preferably tin indium oxide (ITO)；
Glass substrate is preferably selected in element manufacturing of the invention, ITO makees anode material.
The material for constituting the hole transmission layer is Formulas I compound represented；
The material for constituting the organic luminous layer is made of material of main part；
Wherein, the material of main part is any one in following compound:
Constitute any one of the material of the electron transfer layer in following compound:
The material for constituting the electron injecting layer is selected from LiF, Li2O, MgO, Al2O3One of, preferably LiF.
The material for constituting the cathode is selected from one of lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin, preferably aluminium.
Specifically,
The hole transmission layer with a thickness of 10-50nm, preferably 30nm；
The organic luminous layer with a thickness of 10-100nm, preferably 30nm；
The electron transfer layer with a thickness of 10-30nm, preferably 30nm；
The electron injecting layer with a thickness of 5-30nm, preferably 10nm；
The cathode with a thickness of 50-110nm, preferably 60nm.
Novel OLED material provided by the invention is centered on fused ring compound, using (aniline is end group) containing fluorine atom,
By introducing substituent group (N- (2- the fluorophenyl) -9- with hole transport performance in the active position of polycyclc aromatic compound
Phenyl -9H- carbazole -3- amine), obtain a kind of novel OLED material with hole transport performance.Such material has high
Hole mobility, preferable thin film stability and suitable molecular entergy level, can be used in field of organic electroluminescence, as
Hole mobile material uses.
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.
Compound synthesis in the present invention all can refer to the progress of 1 method of embodiment.It is described below in the present invention and partially leads
Want the synthetic method of compound.
Embodiment 1
The synthesis of (compound 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
The 3- bromine-N-phenylcarbazole (purity 99%, 0.2mol) and toluene of fluoroaniline 33.36g (purity 99%, 0.3mol), 63.81g
400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement again.After adding,
It opens agitating and heating and is warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C,
Filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, liquid separation is dried with anhydrous sodium sulfate,
It filters, rotates filtrate, obtain 64.84g yellow product, purity 99%, yield 92%.
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 71.58g
N- (2- fluorophenyl) -9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene composition it is molten
Liquid, 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 anti-with DMF
It boils again several times, obtains 51.75g yellow product, purity 99%, yield 75%.
Product MS (m/e): 879；Elemental analysis (C62H40F2N4): theoretical value C:84.72%, H:4.59%, N:6.37%,
F:4.32%；Measured value C:84.73%, H:5.66%, N:4.60%, F:4.31%.
Embodiment 2
The synthesis of (compound 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
The 3- bromine-N-phenylcarbazole (purity 99%, 0.2mol) and toluene of fluoroaniline 33.36g (purity 99%, 0.3mol), 64.45g
400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement again.After adding,
It opens agitating and heating and is warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C,
Filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, liquid separation is dried with anhydrous sodium sulfate,
It filters, rotates filtrate, obtain 62.02g yellow product, purity 99%, yield 88%.
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
By N- (2- fluorophenyl) -9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene of 71.58g
The solution of 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, filtering, filter cake
It is boiled repeatedly several times with DMF, obtains 50.47g yellow product, purity 99%, yield 72%.
Product MS (m/e): 893.03；Elemental analysis (C63H42F2N4): theoretical value C:84.73%, H:4.74%, F:
4.25%；N:6.27%；Measured value C:84.74%, H:4.73%, F:4.26%；N:6.26%.
Embodiment 3
The synthesis of (compound 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
The 3- bromine-N-phenylcarbazole (purity 99%, 0.2mol) and toluene of fluoroaniline 33.36g (purity 99%, 0.3mol), 64.45g
400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement again.After adding,
It opens agitating and heating and is warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C,
Filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, liquid separation is dried with anhydrous sodium sulfate,
It filters, rotates filtrate, obtain 65.55g yellow product, purity 99%, yield 93%.
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 72.3g's
The solution of N- (2- fluorophenyl) -9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene 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, filtering, filter cake is boiled repeatedly with DMF
Boiling several times, obtains 56.89g yellow product, purity 99%, yield 78%.
Product MS (m/e): 929.06；Elemental analysis (C66H42F2N4): theoretical value C:85.32%, H:4.56%, F:
4.09%；N:6.03%；Measured value C:85.31%, H:4.57%, F:4.10；N:6.02%.
Embodiment 4
(synthesis of compound 4)
Synthetic route is as follows:
Compound 4
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
The 3- bromine-N-phenylcarbazole (purity 99%, 0.2mol) and toluene of fluoroaniline 33.36g (purity 99%, 0.3mol), 64.45g
400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement again.After adding,
It opens agitating and heating and is warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C,
Filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, liquid separation is dried with anhydrous sodium sulfate,
It filters, rotates filtrate, obtain 65.55g yellow product, purity 99%, yield 93%.
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 N- (2- fluorophenyl) -9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml bis- by 72.3g
The solution of toluene 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, filtering,
Filter cake is boiled several times repeatedly with DMF, obtains 53.94g yellow product, purity 99%, yield 78%.
Product MS (m/e): 880.98；Elemental analysis (C60H38F2N6): theoretical value C:81.80%, H:4.35%, F:
4.31%；N:9.54%；Measured value C:81.79%, H:4.36%, F:4.31%；N:9.54%.
Embodiment 5
(synthesis of compound 5)
Synthetic route is as follows:
Compound 5
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
The 3- bromine-N-phenylcarbazole (purity 99%, 0.2mol) and toluene of fluoroaniline 33.36g (purity 99%, 0.3mol), 64.45g
400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement again.After adding,
It opens agitating and heating and is warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C,
Filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, liquid separation is dried with anhydrous sodium sulfate,
It filters, rotates filtrate, obtain 65.55g yellow product, purity 99%, yield 93%.
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
N- (2- fluorophenyl) -9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene of 72.3g forms
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 55.29g yellow product, purity 99%, yield 78%.
Product MS (m/e): 903.03；Elemental analysis (C64H40F2N4): theoretical value C:85.12%, H:4.46%, F:
4.21%；N:6.20%；Measured value C:85.10%, H:4.48%, F:4.21%；N:6.20%.
Embodiment 6
(synthesis of compound 5)
Synthetic route is as follows:
Compound 6
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
The 3- bromine-N-phenylcarbazole (purity 99%, 0.2mol) and toluene of fluoroaniline 33.36g (purity 99%, 0.3mol), 64.45g
400ml.3ml tri-tert-butylphosphine and 0.46g tri- (hexichol benzylacetone) two palladiums are sequentially added after argon gas displacement again.After adding,
It opens agitating and heating and is warming up to 100 DEG C, 100-110 DEG C of temperature control is reacted 5 hours.Filtrate is filtered to obtain through silicagel column after being cooled to 30 DEG C,
Filtrate is rotated, after being dissolved with methylene chloride, is washed twice with 4mol/L hydrochloric acid solution, liquid separation is dried with anhydrous sodium sulfate,
It filters, rotates filtrate, obtain 65.55g yellow product, purity 99%, yield 93%.
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
By N- (2- fluorophenyl) -9- diphenyl -9H- carbazole -3- amine (purity 99%, 0.203mol) and 100ml dimethylbenzene group of 72.3g
At 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 62.28g yellow product, purity 99%, yield 78%.
Product MS (m/e): 1017.17；Elemental analysis (C73H46F2N4): theoretical value C:86.20%, H:4.56%, F:
3.74%；N:5.51%；Measured value C:86.19%, H:4.57%, F:3.74%；N:5.51%.
Technical solution according to embodiment 1-6, it is only necessary to which the corresponding raw material of simple replacement does not change any substantive behaviour
Make, following compound can be synthesized:
Wherein, m is the integer of 1-4.
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 30nm；
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 30nm；
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 10nm；
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；
NPB (control compounds 1)
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, it is characterised in that: its structure is as shown in general formula I:
Wherein, Ar is selected from:
Wherein, m is the integer of 1-4；
It indicates to replace position.
2. organic material according to claim 1, it is characterised in that: in general formula I:
Ar is selected from:
And/or m is 1 or 2.
3. organic material according to claim 1 or 2, it is characterised in that: the organic material is selected from following compound
It is a kind of:
4. the preparation method of the described in any item organic materials of claim 1-3, it is characterised in that: the reaction mechanism mechanism of reaction is as follows:
Include the following steps:
1) using compound 1-1 as starting material, withCoupling reaction occurs, obtains compound 1-2；
2) 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.
5. the preparation method according to claim 4, characterized by the following steps:
1) 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,
Obtain compound I-2；
2) 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. application of the described in any item organic materials of claim 1-3 in organic electroluminescence device.
7. application according to claim 6, it is characterised in that: the organic material is in the organic electroluminescence device
As hole mobile material.
8. a kind of organic electroluminescence device, it is characterised in that: including being made of any one of the claim 1-3 organic material
Hole transmission layer.
9. organic electroluminescence device according to claim 8, it is characterised in that: the organic electroluminescence device is under
It is supreme successively by transparent substrate, anode layer, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and cathode layer
Composition；
Preferably, the material of the transparent substrate is glass substrate or flexible substrate；
And/or；The material of the anode layer is constituted in tin indium oxide, zinc oxide, zinc tin oxide, gold, silver or copper at least
It is a kind of；
And/or；The material of main part of the organic luminous layer is constituted as any one in following compound:
And/or constitute any one of the material of the electron transfer layer in following compound:
And/or；The material for constituting the electron injecting layer is selected from LiF, Li2O, MgO or Al2O3One of；
And/or；The material for constituting the cathode is selected from one of lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin.
10. organic electroluminescence device according to claim 9, it is characterised in that: the hole transmission layer with a thickness of
10-50nm；The organic luminous layer with a thickness of 10-100nm；The electron transfer layer with a thickness of 10-30nm；The electronics
Implanted layer with a thickness of 5-30nm；The cathode with a thickness of 50-110nm.
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