CN109608386A - A kind of organic material and its application in the devices - Google Patents

A kind of organic material and its application in the devices Download PDF

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Publication number
CN109608386A
CN109608386A CN201811506556.2A CN201811506556A CN109608386A CN 109608386 A CN109608386 A CN 109608386A CN 201811506556 A CN201811506556 A CN 201811506556A CN 109608386 A CN109608386 A CN 109608386A
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layer
compound
organic
tri
tert
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张朝霞
段陆萌
李仲庆
郭林林
程丹丹
杭德余
李继响
曹占广
班全志
黄春雪
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Beijing Yanshan Gicom Photoelectric Technology Co Ltd
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Beijing Yanshan Gicom Photoelectric Technology Co Ltd
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    • C07D209/80[b, c]- or [b, d]-condensed
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    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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Abstract

The present invention relates to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical fields, and in particular to a kind of organic material has the structure as shown in general formula I:

Description

A kind of organic material and its application in the devices
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:
M is selected from integer of 1 to 3;
It indicates to replace position.
Material of the present invention can prepare low voltage drive, long-life and efficient OLED element.
Preferably, the Ar are as follows:
M is 1 or 2.
Preferably, the compound is
Organic compound of the present invention is due to containing methyl on phenyl ring, so as to increase intermolecular distance, prevents The only association between compound reduces the probability of molecule piled up, and the organic material is made to have preferable dissolubility and conjunction Crosstalk between pixel will not occur for suitable mobility, reduce the HOMO value of material molecule, and more conducively hole is injected.Thermostabilization Property it is good, when vapor deposition, is less likely to occur to crystallize, and OLED yield rate can be effectively improved by being applied in OLED device, reduces driving electricity Pressure, improves luminous efficiency, increases the service life.
It is specific as follows invention also provides a kind of preferred preparation method of above-mentioned organic compound:
A) using compound 1-1 as starting material, withCoupling reaction occurs, obtains compound 1-2;
B) coupling reaction occurs for 1-2 and dibromo condensed-nuclei aromatics, obtains compound 1;
Wherein, m is integer of 1 to 3, and the Ar refers to identical with specification preceding sections.
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.
It is further preferred that being prepared by the following method:
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, in the protection of nitrogen, 100-110 DEG C of temperature control, compound 1-1 withIt is anti-that coupling occurs It answers, obtains 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, in nitrogen protection, 110-120 DEG C of temperature control, coupling reaction occurs for compound 1-2 and dibromo condensed-nuclei aromatics, obtains compound 1;
Wherein, m is integer of 1 to 3, and the Ar refers to identical with specification preceding sections.The above method is especially suitable In being as Ar
When compound preparation.
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.
It is another object of the present invention to protect organic material of the present invention in preparing organic electroluminescence device Using;
Preferably, the organic material is preparing the application in the hole transmission layer in the organic electroluminescence device.
Final object of the present invention is the organic electroluminescence device that protection contains 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 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 selected from LiF, Li2O, MgO or Al2O3One of, preferably LiF。
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 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 35nm;
And/or the organic luminous layer with a thickness of 10-100nm, preferably 30nm;
And/or the electron transfer layer with a thickness of 10-30nm, preferably 25nm;
And/or the electron injecting layer with a thickness of 5-30nm, preferably 20nm;
And/or the cathode with a thickness of 50-110nm, preferably 70nm.
The invention has the following beneficial effects:
Compound of the present invention is centered on fused ring compound, using methylic aniline as end group, by polycyclic The active position of aromatic compound introduces the substituent group (bis- phenyl -9H- clicks of 4- methyl-N, 9- with hole transport performance Azoles -3- amine), obtain a kind of novel OLED material with hole transport performance.Such material has high hole mobility, Preferable thin film stability, suitable molecular entergy level and higher glass transition temperature can also improve carrier transport effect The luminous efficiency of rate and device can be used in field of organic electroluminescence, use as hole mobile material.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
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
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- 4- methyl -9- phenyl -9H- carbazole of 3- (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 64.11g 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 26.38g (purity 99%, 0.0785mol) and dimethylbenzene 100ml.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 Bis- phenyl -9H- carbazole -3- the amine of 4- methyl-N, 9- (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 54.70g yellow product, purity 99%, yield 80%.
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- 4- methyl -9- phenyl -9H- carbazole of 3- (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 62.72g yellow product, purity 99%, yield 90%.
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 4- 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 52.11g yellow product, purity 99%, yield 75%.
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- 4- methyl -9- phenyl -9H- carbazole of 3- (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 4- 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 61.46g yellow product, purity 99%, yield 85%.
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- 4- methyl -9- phenyl -9H- carbazole of 3- (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 4- 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- 4- methyl -9- phenyl -9H- carbazole of 3- (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 4- 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- 4- methyl -9- phenyl -9H- carbazole of 3- (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 4- 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 M is 2~3.
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 35nm;
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 25nm;
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 20nm;
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 70nm;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.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art 's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed Range.

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:
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
M is 1 or 2.
3. organic material according to claim 1 or 2, which is characterized in that the compound is
4. the preparation method of the described in any item organic materials of claims 1 to 3, which comprises the steps of:
A) using compound 1-1 as starting material, withCoupling reaction occurs, obtains compound 1-2;
B coupling reaction) is occurred with 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. organic material according to claim 4, which is characterized in that be prepared by the following method:
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, in the protection of nitrogen, 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 is alkali, In 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 35nm;
And/or the organic luminous layer with a thickness of 10-100nm, preferably 30nm;
And/or the electron transfer layer with a thickness of 10-30nm, preferably 25nm;
And/or the electron injecting layer with a thickness of 5-30nm, preferably 20nm;
And/or the cathode with a thickness of 50-110nm, preferably 70nm.
CN201811506556.2A 2018-12-10 2018-12-10 A kind of organic material and its application in the devices Withdrawn CN109608386A (en)

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