CN107417668A - A kind of organic compound based on pyridine and benzimidazole and its application on OLED - Google Patents

A kind of organic compound based on pyridine and benzimidazole and its application on OLED Download PDF

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CN107417668A
CN107417668A CN201710330212.XA CN201710330212A CN107417668A CN 107417668 A CN107417668 A CN 107417668A CN 201710330212 A CN201710330212 A CN 201710330212A CN 107417668 A CN107417668 A CN 107417668A
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pyridine
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CN107417668B (en
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张兆超
李崇
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Abstract

The present invention relates to a kind of using pyridine and benzimidazole as the organic compound of core and its application in OLED, the compounds of this invention has higher glass transition temperature and molecule heat endurance；Visible regime absorb it is low, refractive index is high, after the CPL layers applied to OLED, can effectively lift the light extraction efficiency of OLED；The compounds of this invention also has deep HOMO energy levels and high electron mobility, can be as hole barrier/electron transport layer materials of OLED, it can effectively stop that hole or energy are transferred to electronic shell side from luminescent layer, so as to lift the combined efficiency of hole and electronics in luminescent layer, and then lift the luminous efficiency and service life of OLED.

Description

A kind of organic compound based on pyridine and benzimidazole and its on OLED Using
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of using pyridine and benzimidazole as the organic of core Compound and its application on OLED.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used for make New display product is made, can be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is quite varied.OLED luminescent devices are just as the structure of sandwich, including electrode material film layer and are clipped in different electricity Organic functional material between the film layer of pole, various difference in functionality materials are overlapped mutually according to purposes collectively constitutes OLED hairs together Optical device.OLED luminescent devices are as current device, when applying voltage to its two end electrodes, and pass through electric field action organic layer work( Can be in film layer positive and negative charge when, positive and negative charge is further compound in luminescent layer, that is, produces OLED electroluminescent.
Currently, OLED Display Techniques are applied in fields such as smart mobile phone, tablet personal computers, further will also be to electricity Depending on etc. large scale application field extension.But huge spread be present between the external quantum efficiency and internal quantum efficiency due to OLED, Greatly constrain OLED development.Therefore, how to improve OLED light extraction efficiency turns into study hotspot.Ito thin film and glass The interface of the interface of glass substrate and glass substrate and air can be totally reflected, and be emitted to before OLED to exterior space Light account for the 20% of organic material film EL total amounts, it is thin that remaining about 80% light is mainly limited in organic material in the form of guided wave In film, ito thin film and glass substrate.It can be seen that the light extraction efficiency of conventional OLED device is relatively low (about 20%), this is seriously constrained OLED development and application.How to reduce total reflection effect in OLED, improve optically coupling to before device to exterior space Ratio (light extraction efficiency) cause the extensive concern of people.
At present, realize improve OLED external quantum efficiencys a kind of important method be substrate light output surface formed as fold, The structures such as photonic crystal, lenticule display (MLA) and addition surface coating.First two structure can influence OLED radiation spectrum Angular distribution, the third structure fabrication processes are complicated, and use surface coating technique simple, luminous efficiency improve 30% with On, particularly people pay close attention to.According to optical principle, when light transmission superrefraction rate is n1Material to refractive index be n2Material when (n1 ＞ n2), only in arcsin (n2/n1) angle in just to incide refractive index be n2Material in, absorptivity B can be to Under formula calculate：
If n1=nGeneral OLED organic materials=1.70, n2=nGlass=1.46, then 2B=0.49.Assuming that the light whole quilt outwards propagated Metal electrode reflects, then only 51% luminous energy is by the organic film of high index of refraction and the waveguide of ITO layer institute, can equally calculate light from Substrate of glass injects to transmitance during air.When therefore projecting the outside of device from the light that organic layer is sent, only about 17% Luminous energy seen by people.Therefore, for the low present situation of current OLED light extraction efficiency, it is necessary to increase in the device structure Add one layer of CPL layer, i.e. light extraction material, according to optical absorption, refraction principle, the refractive index of this surface coating material should be got over It is high better.
Proposing high performance research to OLED luminescent devices at present includes：Reduce the driving voltage of device, improve the hair of device Light efficiency, the service life for improving device etc..In order to realize the continuous lifting of the performance of OLED, not only need from OLED devices The innovation of part structure and manufacture craft, with greater need for the constantly research and innovation of oled light sulfate ferroelectric functional material, formulate out higher performance OLED functional materials.
The content of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provides one kind using pyridine and benzimidazole as core Organic compound and its application on organic electroluminescence device.The compounds of this invention contains pyridine and benzimidazole knot Structure, there is higher glass transition temperature and molecule heat endurance, visible regime absorb it is low, refractive index is high, applied to After the CPL layers of OLED, the light extraction efficiency of OLED can be effectively lifted,；And because pyridine and benzimidazole have There are deep HOMO energy levels, wide forbidden band (Eg) energy level, can stop as hole barrier/electron transport layer materials of OLED Hole is transferred to electronic shell side from luminescent layer, the multiplicity of hole and electronics in luminescent layer is improved, so as to lift OLED devices The luminous efficiency and service life of part.
Technical scheme is as follows：
The applicant provides a kind of using pyridine and benzimidazole as the organic compound of core, structure such as formula (1) It is shown：
In formula (1), X1~X6Independently be expressed as N atoms or C atoms, and N atoms number is 1 or 2；
Z is numeral 1 or 2；M, n independently be expressed as numeral 0 or 1；And m+n+z=3；
In formula (1), Ar1、Ar2、Ar3Independently be expressed as C1-10Straight or branched alkyl, halogen atom, protium, Deuterium, the substituted or unsubstituted phenyl of tritium atom；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, tritium atom substitution or not Substituted naphthyl；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted dibiphenylyl of tritium atom；Three Xenyl；Anthryl or C1-10In straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted pyridine radicals of tritium atom One kind；Wherein Ar2、Ar3Can also be independently be expressed as singly-bound；
Ar1、Ar2、Ar3Can be with identical or different；
In formula (1), Ar1It is also denoted as formula (2), formula (3), formula (4) or structure shown in formula (5)；
In formula (2), each Y is each independent to be expressed as N or C, and at least one Y is expressed as N；
In formula (3), each Z is each independent to be expressed as N or C, and at least one Z is expressed as N；
In formula (4) and formula (5), R3、R4、R5Independently be expressed as C1-10Straight or branched alkyl, halogen are former Son, protium, deuterium, the substituted or unsubstituted phenyl of tritium atom；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, tritium atom take Generation or unsubstituted naphthyl；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted biphenyl of tritium atom Base；Terphenyl；Anthryl；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted pyridine of tritium atom Base；Dibenzofurans；Dibenzothiophenes；Middle one kind of 9,9- dimethyl fluorenes or N- phenyl carbazoles；
R3、R4、R5Can be with identical or different；
In formula (1), R1、R2Independently be expressed as formula (6), formula (7) or structure shown in formula (8)：
Wherein, Ar4、Ar5、Ar6、Ar7Independently be expressed as C1-10Straight or branched alkyl, halogen atom substitution or not Substituted phenyl, C1-10The substituted or unsubstituted naphthyl of straight or branched alkyl, halogen atom, C1-10Straight or branched alkyl, halogen Plain atom substituted or unsubstituted dibiphenylyl, terphenyl or C1-10Straight or branched alkyl, halogen atom substitution do not take One kind in the pyridine radicals in generation；
R1、R2Can be with identical or different.
Preferably, the concrete structure formula of the organic compound is：
In any one.
The applicant additionally provides a kind of preparation method of described organic compound, the reaction side occurred in preparation process Formula is：
First step course of reaction：
(1) Ar is worked as1When being connected with pyridine with C-C keys,
Specifically course of reaction is：
Under nitrogen atmosphere, weigh raw material A and be dissolved in DMF i.e. DMF, then willAnd vinegar Sour palladium adds, and stirs mixture, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in reaction temperature 120- 5-15 hours are heated to reflux at 150 DEG C；After reaction terminates, cooling Jia Shui, mixture is filtered and dried in vacuum drying chamber, Gained residue crosses silicagel column purifying, obtains compound intermediate I；
The raw material A withMol ratio be 1: 1.0~3, Pd (OAc)2Mol ratio with raw material A is 0.001 ~0.04:1, K3PO4Mol ratio with raw material A is 1.0~4.0:The amount ratio of 1, DMF dosage and raw material A is 1g:10~30ml；
(2) Ar is worked as1When being connected with pyridine with C-N keys,
Specifically course of reaction is：
Weigh raw material A and Ar1- H, dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, sodium tert-butoxide；In inertia Under atmosphere, the mixed solution of above-mentioned reactant is reacted 10~24 hours at 95~110 DEG C of reaction temperature, cools down and filters anti- Solution is answered, filtrate revolving, silicagel column is crossed, obtains intermediate compound I；
The raw material A and Ar1- H mol ratio is 1:1.0~3, Pd2(dba)3With the mol ratio of raw material A for 0.006~ 0.04:1, the mol ratio of tri-butyl phosphine and raw material A is 0.006~0.04:1, the mol ratio of sodium tert-butoxide and raw material A is 2.0 ~3.0:1；
Second step course of reaction：
Under nitrogen atmosphere, weigh intermediate compound I and be dissolved in DMF i.e. DMF, then will And palladium adds, mixture is stirred, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in reaction temperature 10-24 hours are heated to reflux at 120-150 DEG C；After reaction terminates, Jia Shui is cooled down, filter mixture and in vacuum drying chamber Dry, gained residue crosses silicagel column purifying, obtains compound intermediate II；
The intermediate compound I withMol ratio be 1:1.0~3, Pd (OAc)2With the mol ratio of intermediate compound I For 0.001~0.04:1, K3PO4Mol ratio with intermediate compound I is 1.0~4.0:The amount ratio of 1, DMF dosage and intermediate compound I is 1g:10~40ml；
Three-step reaction process：
Under nitrogen atmosphere, weigh intermediate II and be dissolved in DMF i.e. DMF, then will And palladium adds, mixture is stirred, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in reaction temperature 10-24 hours are heated to reflux at 120-150 DEG C；After reaction terminates, Jia Shui is cooled down, filter mixture and in vacuum drying chamber Dry, gained residue crosses silicagel column purifying, obtains target compound；
The intermediate II withMol ratio be 1:1.0~3, Pd (OAc)2With rubbing for intermediate II You are than being 0.001~0.04:1, K3PO4Mol ratio with intermediate II is 1.0~4.0:The use of 1, DMF dosage and intermediate II It is 1g to measure ratio:15~50ml.
The applicant additionally provides a kind of described organic compound using pyridine and benzimidazole as core and is used to make Have organic electroluminescence devices.The applicant additionally provides a kind of illumination or display element, including described organic electroluminescent Device.
The applicant additionally provides a kind of organic electroluminescence device, and the organic electroluminescence device includes at least one layer Functional layer contains the described organic compound using pyridine and benzimidazole as core.
The applicant additionally provides a kind of organic electroluminescence device, including hole blocking layer/electron transfer layer, the sky Cave barrier layer/electron transfer layer contains the described organic compound using pyridine and benzimidazole as core.
The applicant additionally provides a kind of organic electroluminescence device, including CPL layers, the CPL layers contain it is described with Pyridine and the organic compound that benzimidazole is core.
The present invention is beneficial to be had technical effect that：
The structure of the organic compound of the present invention contains two kinds of rigid radicals of pyridine and benzimidazole, improves material knot Structure stability；Material of the present invention is on space structure, and containing strong electro benzimidazole group, and 3 groups are mutually handed over Fork gap is opened, and avoids group from rotating freely so that material has higher density, obtains higher refractive index；Simultaneously so that this Invention material all has very high Tg temperature；The evaporation temperature of material of the present invention under vacuum conditions is generally less than 350 DEG C, both It ensure that material long-time deposition material in volume production does not decompose, reduce again because the heat radiation that temperature is deposited is to being deposited MASK Influence of crust deformation.
Material of the present invention applies the electronics and hole transport in CPL layers, being not involved in device in OLED, but to material Heat endurance, membrane crystallization and optical transport (high index of refraction) there is very high requirement.As above analyze, pyridine and benzo miaow Azoles is rigid radical, improves the stability of material；High Tg temperature, it ensure that material does not crystallize under filminess；Low Temperature is deposited, is the premise that material can be applied to volume production；High refractive index is then that material of the present invention can apply to the most main of CPL layers Want factor.
Material of the present invention high electron mobility, can effectively stop hole or energy from hair due to the HOMO energy levels with depth Photosphere is transferred to electronic shell side, so as to improve the combined efficiency of hole and electronics in luminescent layer, so as to lift OLED Luminous efficiency and service life.After the CPL layers applied to OLED, the light that can effectively lift OLED takes the present invention Go out efficiency.To sum up, compound of the present invention has good application effect and industrialization prospect in OLED luminescent devices.
Brief description of the drawings
Fig. 1 is the materials application cited by the present invention in the structural representation of OLED；Wherein, 1, OLED base Plate, 2, anode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, hole blocking layer/electron transfer layer, 7, electronics Implanted layer, 8, cathode layer, 9, CPL layers.
Fig. 2 is the refraction index test figure of compound 76；Fig. 3 is compound 70 and well known materials CBP film Acceleration study pair Than figure.
Embodiment
Embodiment 1：The synthesis of intermediate compound I
When pyridine and Ar1When being connected with C-C keys,
Under nitrogen atmosphere, Ar is weighed1Bromo-derivative is dissolved in tetrahydrofuran (THF), then double (pinacol foundation) two boron of general, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate add, and stir mixture, by the mixed of above-mentioned reactant Close solution and be heated to reflux 5-10 hours at 70-90 DEG C of reaction temperature；After reaction terminates, add water cooling and filter mixture And dried in vacuum drying oven.The residue obtained is crossed into silica gel column separating purification, obtains Ar1Pinacol borate；
Under nitrogen atmosphere, weigh raw material A and be dissolved in DMF i.e. DMF, then willAnd vinegar Sour palladium adds, and stirs mixture, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in reaction temperature 120- 5-15 hours are heated to reflux at 150 DEG C；After reaction terminates, cooling Jia Shui, mixture is filtered and dried in vacuum drying chamber, Gained residue crosses silicagel column purifying, obtains compound intermediate I；
The raw material A withMol ratio be 1:1.0~3, Pd (OAc)2Mol ratio with raw material A is 0.001 ~0.04:1, K3PO4Mol ratio with raw material A is 1.0~4.0:The amount ratio of 1, DMF dosage and raw material A is 1g：10~30ml；
When pyridine and Ar1When being connected with C-N keys,
Weigh raw material A and Ar1- H, dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, sodium tert-butoxide；In inertia Under atmosphere, the mixed solution of above-mentioned reactant is reacted 10~24 hours at 95~110 DEG C of reaction temperature, cools down and filters anti- Solution is answered, filtrate revolving, silicagel column is crossed, obtains intermediate compound I；
The raw material A and Ar1- H mol ratio is 1:1.0~3, Pd2(dba)3With the mol ratio of raw material A for 0.006~ 0.04:1, the mol ratio of tri-butyl phosphine and raw material A is 0.006~0.04:1, the mol ratio of sodium tert-butoxide and raw material A is 2.0 ~3.0:1；
By taking the synthesis of intermediate A 1 as an example
(1) in 250mL there-necked flasks, nitrogen is passed through, adds 0.02mol 4- bromo- 1,1 '-biphenyl is dissolved in 100ml tetrahydrochysenes In furans (THF), then by 0.024mol double (pinacol foundation) two boron, 0.0002mol (1,1’- bis- (diphenylphosphine) ferrocene) Dichloro palladium (II) and 0.05mol potassium acetates add, and mixture are stirred, by the mixed solution of above-mentioned reactant in reaction temperature 80 It is heated to reflux at DEG C 5 hours；After reaction terminates, cool down and add 100ml water and mixture is filtered and done in vacuum drying oven It is dry.The residue obtained is crossed into silica gel column separating purification, obtains 4- biphenylboronic acid pinacol esters；HPLC purity 99.9%, receive Rate 92.7%.
Elementary analysis structure (molecular formula C18H21BO2)：Theoretical value C, 77.17；H,7.55；B,3.86；O,11.42；Test Value：C,77.16；H,7.54；B,3.87；O,11.43.ESI-MS(m/z)(M+)：Theoretical value 280.16, measured value are 280.52。
(2) in 250mL there-necked flasks, nitrogen is passed through, adds bromo- 2, the 6- dichloropyridines of 0.02mol raw materials 4-, 150mlDMF, 0.024mol 4- biphenylboronic acid pinacol esters, 0.0002mol palladiums, stirring, then add 0.03mol K3PO4The aqueous solution, 130 DEG C are heated to, back flow reaction 10 hours, sample point plate, reaction is completely.Natural cooling, Jia Shui, it will mix Thing is filtered and dried in vacuum drying chamber, and gained residue crosses silicagel column purifying, obtains compound intermediate A1；HPLC purity 99.5%, yield 88.3%.
Elementary analysis structure (molecular formula C17H11Cl2N)：Theoretical value C, 68.02；H,3.69；Cl,23.62；N,4.67；Survey Examination value：C,68.04；H,3.68；Cl,23.63；N,4.65.ESI-MS(m/z)(M+)：Theoretical value 299.03, measured value are 299.41。
By taking the synthesis of intermediate A 14 as an example
250ml there-necked flask, under the atmosphere for being passed through nitrogen, bromo- 4, the 6- dichloro pyrimidines of 0.01mol 2- are added, 0.015mol N- phenyl-【1,1 '-biphenyl】- 4- amine, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10- 4Mol tri-butyl phosphines, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete；Natural cooling, filtering, filtrate Revolving, silicagel column is crossed, obtains intermediate A 14, HPLC purity 99.5%, yield 82.7%.
Elementary analysis structure (molecular formula C22H15Cl2N3)：Theoretical value C, 67.36；H,3.85；Cl,18.08；N,10.71； Test value：C,67.35；H,3.84；Cl,18.09；N,10.72.ESI-MS(m/z)(M+)：Theoretical value 391.06, measured value For 391.06.
Intermediate compound I is prepared with intermediate A 1, A14 synthetic method, concrete structure is as shown in table 1.
Table 1
Embodiment 2：IntermediateSynthesis
Work as R1Or R2When being expressed as formula (6) structure,
(1) in 250mL there-necked flasks, nitrogen is passed through, adds the bromo- benzimidazoles of 0.02mol raw materials 2-, 0.03mol I- Ar4, 0.04mol sodium hydrides, 0.004mol cuprous iodides and 0.01mol Phens be dissolved in 100ml 1,3- dimethyl -2- In imidazolone, stirring reaction 20-30h, after reaction terminates, add water and extracted with dichloromethane, organic layer anhydrous sodium sulfate Dry, the mixture with petroleum ether and ethyl acetate is the volume ratio of eluent elution, eluent petrochina ether and ethyl acetate For 1:100, column chromatography purifying, obtain intermediate M；
(2) under nitrogen atmosphere, weigh intermediate M and be dissolved in tetrahydrofuran, then by Br-Ar2-B(OH)2And four (triphenyl Phosphine) palladium addition, mixture is stirred, unsaturated carbonate aqueous solutions of potassium is added, by the mixed solution of above-mentioned reactant in reaction temperature 10-20 hours are heated to reflux at 70-90 DEG C；After reaction terminates, cooling, mixed liquor are extracted with dichloromethane, and extract is with anhydrous Sodium sulphate drying process, and concentrate under reduced pressure, thickened solid is crossed into silicagel column purifying, obtains compound intermediate N；
(3) under nitrogen atmosphere, weigh intermediate N and be dissolved in DMF (DMF), then will double (pinacols Foundation) two boron, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate add, and stirs mixture, and will be above-mentioned The mixed solution of reactant is heated to reflux 5-10 hours at 120-150 DEG C of reaction temperature；After reaction terminates, cool down and will mix Compound is filtered and dried in vacuum drying oven.The residue obtained is crossed into silica gel column separating purification, obtains compound intermediate IV；
Work as R1Or R2When being expressed as formula (7) structure,
(1) under nitrogen atmosphere, the bromo- benzimidazoles of 2- is weighed and are dissolved in tetrahydrofuran, then by Ar5-B(OH)2And four (three Phenylphosphine) palladium addition, mixture is stirred, unsaturated carbonate aqueous solutions of potassium is added, by the mixed solution of above-mentioned reactant in reaction 5-15 hours are heated to reflux at 70-90 DEG C of temperature；After reaction terminates, cooling, mixed liquor are extracted with dichloromethane, extract nothing Aqueous sodium persulfate drying process, and concentrate under reduced pressure, thickened solid is crossed into silicagel column purifying, obtains compound intermediate P；
(2) under nitrogen atmosphere, intermediate P, I-Ar are added2- Br, sodium hydride, cuprous iodide and Phen are dissolved in 1, In 3- dimethyl-2-imidazolinones, stirring reaction 20-30h, after reaction terminates, add water and extracted with dichloromethane, organic layer is used Anhydrous sodium sulfate drying, the mixture with petroleum ether and ethyl acetate are eluent elution, column chromatography purifying, obtain intermediate Q；
(3) under nitrogen atmosphere, weigh intermediate Q and be dissolved in DMF (DMF), then will double (pinacols Foundation) two boron, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate add, and stirs mixture, and will be above-mentioned The mixed solution of reactant is heated to reflux 5-10 hours at 120-150 DEG C of reaction temperature；After reaction terminates, cool down and will mix Compound is filtered and dried in vacuum drying oven.The residue obtained is crossed into silica gel column separating purification, obtains compound intermediate IV；
Work as R1Or R2When being expressed as formula (8) structure,
(1) under nitrogen atmosphere, raw material W, I-Ar are added7, sodium hydride, cuprous iodide and Phen be dissolved in 1,3- diformazans In base -2- imidazolones, stirring reaction 20-30h, after reaction terminates, add water and extracted with dichloromethane, the anhydrous sulphur of organic layer Sour sodium is dried, and the mixture with petroleum ether and ethyl acetate is eluent elution, column chromatography purifying, obtains intermediate X；
(2) under nitrogen atmosphere, weigh intermediate X and be dissolved in tetrahydrofuran, then by Ar6-B(OH)2And four (triphenylphosphine) Palladium adds, and stirs mixture, unsaturated carbonate aqueous solutions of potassium is added, by the mixed solution of above-mentioned reactant in reaction temperature 70- 5-15 hours are heated to reflux at 90 DEG C；After reaction terminates, cooling, mixed liquor are extracted with dichloromethane, extract anhydrous slufuric acid Sodium drying process, and concentrate under reduced pressure, thickened solid is crossed into silicagel column purifying, obtains compound intermediate Y；
(3) under nitrogen atmosphere, weigh intermediate Y and be dissolved in DMF, then by Br-Ar2-B(OH)2And Palladium adds, and stirs mixture, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in reaction temperature 120- 10-24 hours are heated to reflux at 150 DEG C；After reaction terminates, cooling Jia Shui, mixture is filtered and done in vacuum drying chamber Dry, gained residue crosses silicagel column purifying, obtains Compound Compound intermediate Z；
(4) under nitrogen atmosphere, weigh intermediate Z and be dissolved in DMF (DMF), then will double (pinacols Foundation) two boron, (1,1 '-bis- (diphenylphosphine) ferrocene) dichloro palladium (II) and potassium acetate add, and stirs mixture, and will be above-mentioned The mixed solution of reactant is heated to reflux 5-10 hours at 120-150 DEG C of reaction temperature；After reaction terminates, cool down and will mix Compound is filtered and dried in vacuum drying oven.The residue obtained is crossed into silica gel column separating purification, obtains compound intermediate IV；
By taking the synthesis of intermediate B 1 as an example
(1) in 250mL there-necked flasks, nitrogen is passed through, adds the bromo- 1H- benzimidazoles of 0.02mol raw materials 2-, 0.03mol iodine Benzene, 0.04mol sodium hydrides, 0.004mol cuprous iodides and 0.01mol Phens are dissolved in 100ml 1,3- dimethyl -2- miaows In oxazoline ketone, stirring reaction 20-30h, after reaction terminates, add water and extracted with dichloromethane, organic layer is done with anhydrous sodium sulfate Dry, the mixture with petroleum ether and ethyl acetate is that eluent elutes, and the volume ratio of eluent petrochina ether and ethyl acetate is 1:100, column chromatography purifying, obtain intermediate M1；HPLC purity 99.5%, yield 75.8%.
Elementary analysis structure (molecular formula C13H9BrN2)：Theoretical value C, 57.17；H,3.32；Br,29.26；N,10.26；Survey Examination value：C,57.18；H,3.33；Br,29.25；N,10.24.ESI-MS(m/z)(M+)：Theoretical value 271.99, measured value are 272.32。
(2) in 250mL there-necked flasks, nitrogen is passed through, adds 0.04mol intermediates M1,100mlTHF, 0.05mol benzene boron Acid, 0.0004mol tetrakis triphenylphosphine palladiums, stirring, then add 0.06mol K2CO3The aqueous solution (2M), is heated to 80 DEG C, returns Stream reaction 10 hours, sample point plate, reaction are complete.Natural cooling, extracted with 200ml dichloromethane, layering, extract is with anhydrous Sodium sulphate is dried, filtering, filtrate revolving, is crossed silicagel column purifying, is obtained intermediate N1, HPLC purity 99.6%, yield 84.9%.
Elementary analysis structure (molecular formula C19H13BrN2)：Theoretical value C, 65.35；H,3.75；Br,22.88；N,8.02；Survey Examination value：C,65.36；H,3.74；Br,22.89；N,8.03.ESI-MS(m/z)(M+)：Theoretical value 348.03, measured value are 348.45。
(3) in 500mL there-necked flasks, nitrogen is passed through, 0.05 intermediate N1 is added and is dissolved in 300mlN, N- dimethyl formyls In amine (DMF), then by double (pinacol foundation) two boron of 0.06mol, 0.0005mol (1,1 '-bis- (diphenylphosphine) ferrocene) two Chlorine palladium (II) and 0.125mol potassium acetates add, and mixture are stirred, by the mixed solution of above-mentioned reactant in reaction temperature It is heated to reflux at 120-150 DEG C 10 hours；After reaction terminates, cool down and add 200ml water and filter mixture and in vacuum Dried in baking oven.The residue obtained is crossed into silica gel column separating purification, obtains compound intermediate B1；HPLC purity 99.5%, yield 84.1%.
Elementary analysis structure (molecular formula C25H25BN2O2)：Theoretical value C, 75.77；H,6.36；B,2.73；N,7.07；O, 8.07；Test value：C,75.79；H,6.35；B,2.72；N,7.08；O,8.06.ESI-MS(m/z)(M+)：Theoretical value 396.20 measured value 396.62.Intermediate compound IV is prepared with the synthetic method of intermediate B 1, concrete structure is as shown in table 2.
Table 2
Embodiment 3：The synthesis of compound 3：
In 250mL there-necked flasks, nitrogen is passed through, adds 0.01mol intermediate As 1,150mlDMF, 0.03mol intermediates B1,0.0002mol palladium, stirring, then add 0.02mol K3PO4The aqueous solution, 150 DEG C are heated to, back flow reaction 24 is small When, sample point plate, reaction is completely.Natural cooling, extracted with 200ml dichloromethane, layering, extract is done with anhydrous sodium sulfate It is dry, filtering, filtrate revolving, silicagel column purifying is crossed, obtains target product, HPLC purity 99.4%, yield 64.7%.
Elementary analysis structure (molecular formula C55H37N5)：Theoretical value C, 86.02；H,4.86；N,9.12；Test value：C, 86.05；H,4.85；N,9.10.ESI-MS(m/z)(M+)：Theoretical value 767.30, measured value 767.58.
Embodiment 4：The synthesis of compound 9：
In 250mL there-necked flasks, nitrogen is passed through, adds 0.01mol intermediate As 2,150mlDMF, 0.03mol intermediates B1,0.0002mol palladium, stirring, then add 0.02mol K3PO4The aqueous solution, 150 DEG C are heated to, back flow reaction 24 is small When, sample point plate, reaction is completely.Natural cooling, extracted with 200ml dichloromethane, layering, extract is done with anhydrous sodium sulfate It is dry, filtering, filtrate revolving, silicagel column purifying is crossed, obtains target product, HPLC purity 99.1%, yield 67.2%.
Elementary analysis structure (molecular formula C53H35N5)：Theoretical value C, 85.80；H,4.76；N,9.44；Test value：C, 85.80；H,4.75；N,9.45.ESI-MS(m/z)(M+)：Theoretical value 741.29, measured value 741.72.
Embodiment 5：The synthesis of compound 10：
With embodiment 3, difference is to replace intermediate A 1 with intermediate A 3 preparation method of compound 10.Element point Analyse structure (molecular formula C53H35N5)：Theoretical value C, 85.80；H,4.76；N,9.44；Test value：C,85.80；H,4.77；N, 9.43。ESI-MS(m/z)(M+)：Theoretical value 741.29, measured value 741.73.
Embodiment 6：The synthesis of compound 22：
With embodiment 3, difference is to replace intermediate A 1 with intermediate A 4 preparation method of compound 22.Element point Analyse structure (molecular formula C58H41N5)：Theoretical value C, 86.22；H,5.11；N,8.67；Test value：C,86.24；H,5.10；N, 8.66。ESI-MS(m/z)(M+)：Theoretical value 807.34, measured value 807.75.
Embodiment 7：The synthesis of compound 25：
With embodiment 3, difference is to replace intermediate A 1 with intermediate A 5 preparation method of compound 25.Element point Analyse structure (molecular formula C61H42N6)：Theoretical value C, 85.29；H,4.93；N,9.78；Test value：C,85.31；H,4.92；N, 9.77。ESI-MS(m/z)(M+)：Theoretical value 858.35, measured value 858.69.
Embodiment 8：The synthesis of compound 29：
The preparation method of compound 29 is with embodiment 3, and difference is to replace intermediate A 1 with intermediate A 6, with centre Body B2 replaces intermediate B 1.Elementary analysis structure (molecular formula C61H40N6)：Theoretical value C, 85.49；H,4.70；N,9.81；Test Value：C,85.47；H,4.71；N,9.82.ESI-MS(m/z)(M+)：Theoretical value 856.33, measured value 856.74.
Embodiment 9：The synthesis of compound 41：
In 250mL there-necked flasks, nitrogen is passed through, adds 0.01mol intermediate As 7,150mlDMF, 0.015mol intermediates B1,0.0001mol palladium, stirring, then add 0.01mol K3PO4The aqueous solution, 150 DEG C are heated to, back flow reaction 24 is small When, sample point plate, reaction is completely.Natural cooling, extracted with 200ml dichloromethane, layering, extract is done with anhydrous sodium sulfate It is dry, filtering, filtrate revolving, silicagel column purifying is crossed, obtains target product, HPLC purity 99.6%, yield 67.2%.
Elementary analysis structure (molecular formula C46H31N5)：Theoretical value C, 84.51；H,4.78；N,10.71；Test value：C, 84.51；H,4.77；N,10.72.ESI-MS(m/z)(M+)：Theoretical value 653.26, measured value 653.68.
Embodiment 10：The synthesis of compound 44：
The preparation method of compound 44 is with embodiment 9, and difference is to replace intermediate A 1 with intermediate A 8, with centre Body B3 replaces intermediate B 1.Elementary analysis structure (molecular formula C48H31N5)：Theoretical value C, 85.06；H,4.61；N,10.33；Test Value：C,85.06；H,4.62；N,10.32.ESI-MS(m/z)(M+)：Theoretical value 677.26, measured value 677.65.
Embodiment 11：The synthesis of compound 58：
With embodiment 9, difference is to replace intermediate A 7 with intermediate A 9 preparation method of compound 58.Element point Analyse structure (molecular formula C56H39N9)：Theoretical value C, 80.27；H,4.69；N,15.04；Test value：C,80.28；H,4.70；N, 15.02。ESI-MS(m/z)(M+)：Theoretical value 837.33, measured value 837.70.
Embodiment 12：The synthesis of compound 70：
With embodiment 3, difference is to replace intermediate A 1 with intermediate A 10 preparation method of compound 70.Element Analytical structure (molecular formula C54H36N6)：Theoretical value C, 84.35；H,4.72；N,10.93；Test value：C,84.35；H,4.73；N, 10.92。ESI-MS(m/z)(M+)：Theoretical value 768.30, measured value 768.67.
Embodiment 13：The synthesis of compound 76：
With embodiment 3, difference is to replace intermediate A 1 with intermediate A 11 preparation method of compound 76.Element Analytical structure (molecular formula C52H34N6)：Theoretical value C, 84.07；H,4.61；N,11.31；Test value：C,84.08；H,4.60； N,11.32。ESI-MS(m/z)(M+)：Theoretical value 742.28, measured value 742.59.
Embodiment 14：The synthesis of compound 81：
With embodiment 3, difference is to replace intermediate A 1 with intermediate A 12 preparation method of compound 81.Element Analytical structure (molecular formula C51H33N7)：Theoretical value C, 82.35；H,4.47；N,13.18；Test value：C,82.33；H,4.48；N, 13.19。ESI-MS(m/z)(M+)：Theoretical value 743.28, measured value 743.61.
Embodiment 15：The synthesis of compound 88：
With embodiment 3, difference is to replace intermediate A 1 with intermediate A 13 preparation method of compound 88.Element Analytical structure (molecular formula C60H39N7)：Theoretical value C, 83.99；H,4.58；N,11.43；Test value：C,83.98；H,4.57；N, 11.45。ESI-MS(m/z)(M+)：Theoretical value 857.33, measured value 857.69.
Embodiment 16：The synthesis of compound 90：
In 250mL there-necked flasks, nitrogen is passed through, adds 0.01mol intermediate As 14,150mlDMF, 0.03mol intermediates B1,0.0002mol palladium, stirring, then add 0.02mol K3PO4The aqueous solution, 150 DEG C are heated to, back flow reaction 24 is small When, sample point plate, reaction is completely.Natural cooling, extracted with 200ml dichloromethane, layering, extract is done with anhydrous sodium sulfate It is dry, filtering, filtrate revolving, silicagel column purifying is crossed, obtains target product, HPLC purity 99.3%, yield 65.4%.
Elementary analysis structure (molecular formula C60H41N7)：Theoretical value C, 83.79；H,4.81；N,11.40；Test value：C, 83.77；H,4.82；N,11.41.ESI-MS(m/z)(M+)：Theoretical value 859.34, measured value 859.72.
Embodiment 17：The synthesis of compound 97：
The preparation method of compound 97 is with embodiment 3, and difference is to replace intermediate A 1 with intermediate A 15, in Mesosome B2 replaces intermediate B 1.Elementary analysis structure (molecular formula C50H32N8)：Theoretical value C, 80.63；H,4.33；N,15.04；Survey Examination value：C,80.60；H,4.35；N,15.05.ESI-MS(m/z)(M+)：Theoretical value 744.27, measured value 744.68.
Embodiment 18：The synthesis of compound 104：
The preparation method of compound 104 is with embodiment 9, and difference is to replace intermediate A 7 with intermediate A 16, in Mesosome B4 replaces intermediate B 1.Elementary analysis structure (molecular formula C53H36N4)：Theoretical value C, 87.33；H,4.98；N,7.69；Survey Examination value：C,87.31；H,4.99；N,7.70.ESI-MS(m/z)(M+)：Theoretical value 728.29, measured value 728.66.
Embodiment 19：The synthesis of compound 110：
The preparation method of compound 110 is with embodiment 9, and difference is to replace intermediate A 7 with intermediate A 17, in Mesosome B3 replaces intermediate B 1.Elementary analysis structure (molecular formula C45H28N8)：Theoretical value C, 86.96；H,4.77；N,8.28；Survey Examination value：C,86.98；H,4.75；N,8.27.ESI-MS(m/z)(M+)：Theoretical value 680.24, measured value 680.65.
Embodiment 20：The synthesis of compound 112：
With embodiment 19, difference is to replace intermediate A 17 with intermediate A 18 preparation method of compound 112.Member Plain analytical structure (molecular formula C47H30N6)：Theoretical value C, 83.16；H,4.45；N,12.38；Test value：C,83.19；H,4.45； N,12.36。ESI-MS(m/z)(M+)：Theoretical value 678.25, measured value 678.71.
Embodiment 21：The synthesis of compound 126：
With embodiment 9, difference is to replace intermediate A 7 with intermediate A 19 preparation method of compound 126.Element Analytical structure (molecular formula C55H38N10)：Theoretical value C, 78.74；H,4.57；N,16.70；Test value：C,78.71；H,4.58；N, 16.71。ESI-MS(m/z)(M+)：Theoretical value 838.33, measured value 838.72.
Embodiment 22：The synthesis of compound 144：
In 250mL there-necked flasks, nitrogen is passed through, adds 0.01mol intermediate As 20,150mlDMF, 0.012mol intermediates B1,0.0001mol palladium, stirring, then add 0.01mol K3PO4The aqueous solution, 150 DEG C are heated to, back flow reaction 24 is small When, sample point plate, reaction is completely.Natural cooling, extracted with 200ml dichloromethane, layering, extract is done with anhydrous sodium sulfate It is dry, filtering, filtrate revolving, silicagel column purifying is crossed, obtains intermediate C1, HPLC purity 99.2%0, yield 85.1%.
Elementary analysis structure (molecular formula C29H19ClN4)：Theoretical value C, 75.89；H,4.17；Cl,7.72；N,12.21；Survey Examination value：C,75.91；H,4.16；Cl,7.73；N,12.20.ESI-MS(m/z)(M+)：Theoretical value 458.13, measured value are 458.53。
In 250mL there-necked flasks, nitrogen is passed through, adds 0.01mol intermediates C1,150mlDMF, 0.015mol intermediate B5,0.0001mol palladium, stirring, then add 0.01mol K3PO4The aqueous solution, 150 DEG C are heated to, back flow reaction 24 is small When, sample point plate, reaction is completely.Natural cooling, extracted with 200ml dichloromethane, layering, extract is done with anhydrous sodium sulfate It is dry, filtering, filtrate revolving, silicagel column purifying is crossed, obtains target product, HPLC purity 99.5%, yield 71.7%.
Elementary analysis structure (molecular formula C48H32N6)：Theoretical value C, 83.21；H,4.66；N,12.13；Test value：C, 83.21；H,4.68；N,12.11.ESI-MS(m/z)(M+)：Theoretical value 692.27, measured value 692.66.
The organic compound of the present invention uses in luminescent device, as CPL layer materials, has high Tg (gamma transitions Temperature) temperature, high index of refraction.The compound prepared to embodiment carries out the test of hot property and refractive index, testing result respectively As shown in table 3, wherein Fig. 2 is the refraction index test figure of compound 76.
Table 3
Note：Glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi companies DSC204F1 differential scanning calorimetries Instrument) measure, 10 DEG C/min of heating rate；Refractive index is by ellipsometer (U.S.'s J.A.Woollam Co. models：ALPHA-SE) survey Amount, is tested as atmospheric environment.
From upper table data, the materials such as CBP, Alq3 and the TPBi applied at present, organic compound of the invention are contrasted With high glass transition temperature, high index of refraction, simultaneously because containing pyridine and benzimidazole rigid radical, material ensure that Heat endurance.Therefore, the present invention is the organic material of core in the CPL applied to OLED using pyridine and benzimidazole After layer, the light extraction efficiency of device can be effectively improved, and ensure that the long-life of OLED.
The OLED material of the invention synthesized is described in detail in device below by way of device embodiments 1~21 and device comparative example 1 Application effect in part.Device embodiments 2~21 of the present invention, the device compared with device embodiments 1 of device comparative example 1 Manufacture craft it is identical, and employed identical baseplate material and electrode material, the thickness of electrode material are also kept Unanimously, except that the CPL layer materials in 2~18 pairs of devices of device embodiments convert；19~21 pairs of device embodiments Hole barrier/electron transport layer materials of device convert, the performance test results such as institute of table 4 of each embodiment obtained device Show.
Device embodiments 1：As shown in figure 1, a kind of electroluminescent device, its preparation process includes：
A) the ito anode layer 2 cleaned on transparent OLED device substrate 1 is clear with deionized water, acetone, EtOH Sonicate respectively Wash each 15 minutes, then handled 2 minutes in plasma cleaner；B) on ito anode layer 2, vacuum evaporation mode is passed through Hole injection layer material HAT-CN is deposited, thickness 10nm, this layer is as hole injection layer 3；C) on hole injection layer 3, lead to Cross vacuum evaporation mode and hole mobile material NPB, thickness 80nm is deposited, the layer is hole transmission layer 4；D) in hole transmission layer Luminescent layer 5 is deposited on 4, CBP is used as material of main part, Ir (ppy)3As dopant material, Ir (ppy)3With CBP quality Than for 1: 9, thickness 30nm；E) on luminescent layer 5, electron transport material TPBI, thickness are deposited by vacuum evaporation mode For 40nm, this layer of organic material uses as hole barrier/electron transfer layer 6；F) on hole barrier/electron transfer layer 6, Vacuum evaporation electron injecting layer LiF, thickness 1nm, the layer is electron injecting layer 7；G) on electron injecting layer 7, vacuum is steamed Plate negative electrode Mg：Ag/Ag layers, Mg:Ag doping ratios are 9:1, thickness 15nm, Ag thickness 3nm, the layer are cathode layer 8；H) in negative electrode On layer 8, CPL material compounds 3 are deposited by vacuum evaporation mode, thickness 50nm, this layer of organic material is as CPL layers 9 Use.
After the making that electroluminescent device is completed according to above-mentioned steps, the current efficiency of measurement device and life-span, its result It is shown in Table 4.The molecular machinery formula of associated materials is as follows：
Device embodiments 2：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 9.Device embodiments 3：It is electroluminescent The CPL layer materials of luminescent device are changed into the compounds of this invention 10.Device embodiments 4：The CPL layer materials of electroluminescent device are changed into The compounds of this invention 22.Device embodiments 5：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 25.Device is implemented Example 6：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 29.Device embodiments 7：The CPL layers of electroluminescent device Material is changed into the compounds of this invention 41.Device embodiments 8：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 44. Device embodiments 9：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 58.Device embodiments 10：Electroluminescent cell The CPL layer materials of part are changed into the compounds of this invention 70.Device embodiments 11：The CPL layer materials of electroluminescent device are changed into this hair Bright compound 76.Device embodiments 12：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 81.Device embodiments 13：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 88.Device embodiments 14：The CPL layers of electroluminescent device Material is changed into the compounds of this invention 90.Device embodiments 15：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 97.Device embodiments 16：The CPL layer materials of electroluminescent device are changed into the compounds of this invention 104.Device embodiments 17：It is electroluminescent The CPL layer materials of luminescent device are changed into the compounds of this invention 110.Device embodiments 18：The CPL layer materials of electroluminescent device become For the compounds of this invention 112.Device embodiments 19：Hole barrier/electron transport layer materials of electroluminescent device are changed into this hair Bright compound 41.Device embodiments 20：Hole barrier/electron transport layer materials of electroluminescent device are changed into the compounds of this invention 58.Device embodiments 21：Hole barrier/electron transport layer materials of electroluminescent device are changed into the compounds of this invention 126.Device Comparative example 1：The CPL layer materials of electroluminescent device are changed into well known materials Alq3.The detection data of gained electroluminescent device are shown in Shown in table 4.
Table 4
Organic compound application of the present invention using pyridine and benzimidazole as core can be seen that by the result of table 4 After the making of OLED luminescent devices, compared with device comparative example 1, light, which takes out, to be obviously improved, under same current density, device Brightness and device efficiency are obtained for lifting, because brightness and efficiency get a promotion, power consumption phase of the OLED in the case where determining brightness To reducing, service life is also improved.
In order to illustrate material membrane phase crystallization-stable performance of the present invention, by material compound 70 of the present invention and well known materials CBP has carried out film and has accelerated crystallization experiment：Using vacuum evaporation mode, it is deposited respectively and compound 70 and CBP is vaporized on alkali-free glass On glass, and it is packaged in glove box (water oxygen content ＜ 0.1ppm), by sample after encapsulation in double 85 (85 DEG C of temperature, humidity 85%) placed under the conditions of, the crystalline state of material membrane periodically observed with microscope (LEICA, DM8000M, 5*10 multiplying power), Experimental result is as shown in table 5, and material surface form is as shown in Figure 3.
Table 5
Title material Compound 70 CBP
After material filming Smooth surface morphology even uniform Smooth surface morphology even uniform
After experiment 72 hours Smooth surface morphology even uniform, nodeless mesh Surface forms some scattered circular crystal planes
After experiment 600 hours Smooth surface morphology even uniform, nodeless mesh Surface checking
Above description of test, the membrane crystallization stability of material of the present invention is significantly larger than well known materials, applied to OLED devices Service life after part has beneficial effect.

Claims (8)

  1. A kind of 1. organic compound using pyridine and benzimidazole as core, it is characterised in that the knot of the organic compound Shown in structure such as formula (1)：
    In formula (1), X1~X6Independently be expressed as N atoms or C atoms, and N atoms number is 1 or 2；
    Z is numeral 1 or 2；M, n independently be expressed as numeral 0 or 1；And m+n+z=3；
    In formula (1), Ar1、Ar2、Ar3Independently be expressed as C1-10Straight or branched alkyl, halogen atom, protium, deuterium, tritium are former The substituted or unsubstituted phenyl of son；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted naphthalene of tritium atom Base；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted dibiphenylyl of tritium atom；Terphenyl；Anthracene Base or C1-10Straight or branched alkyl, halogen atom, protium, deuterium, middle one kind of the substituted or unsubstituted pyridine radicals of tritium atom；Its Middle Ar2、Ar3Can also be independently be expressed as singly-bound；
    Ar1、Ar2、Ar3Can be with identical or different；
    In formula (1), Ar1It is also denoted as formula (2), formula (3), formula (4) or structure shown in formula (5)；
    In formula (2), each Y is each independent to be expressed as N or C, and at least one Y is expressed as N；
    In formula (3), each Z is each independent to be expressed as N or C, and at least one Z is expressed as N；
    In formula (4) and formula (5), R3、R4、R5Independently be expressed as C1-10Straight or branched alkyl, halogen atom, protium, Deuterium, the substituted or unsubstituted phenyl of tritium atom；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, tritium atom substitution or not Substituted naphthyl；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted dibiphenylyl of tritium atom；Three Xenyl；Anthryl；C1-10Straight or branched alkyl, halogen atom, protium, deuterium, the substituted or unsubstituted pyridine radicals of tritium atom；Hexichol And furans；Dibenzothiophenes；Middle one kind of 9,9- dimethyl fluorenes or N- phenyl carbazoles；
    R3、R4、R5Can be with identical or different；
    In formula (1), R1、R2Independently be expressed as formula (6), formula (7) or structure shown in formula (8)：
    Wherein, Ar4、Ar5、Ar6、Ar7Independently be expressed as C1-10Straight or branched alkyl, halogen atom substitution or unsubstituted Phenyl, C1-10The substituted or unsubstituted naphthyl of straight or branched alkyl, halogen atom, C1-10Straight or branched alkyl, halogen are former Son substituted or unsubstituted dibiphenylyl, terphenyl or C1-10Straight or branched alkyl, halogen atom are substituted or unsubstituted One kind in pyridine radicals；
    R1、R2Can be with identical or different.
  2. 2. organic compound according to claim 1, it is characterised in that the concrete structure formula of the organic compound is：
    In any one.
  3. 3. the preparation method of the organic compound described in a kind of claim 1 or 2, it is characterised in that occur in preparation process Reaction equation is：
    First step course of reaction：
    (1) Ar is worked as1When being connected with pyridine with C-C keys,
    Equation (1) is answered in first contragradience
    Specifically course of reaction is：
    Under nitrogen atmosphere, weigh raw material A and be dissolved in DMF i.e. DMF, then willAnd palladium adds Enter, stir mixture, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant at 120-150 DEG C of reaction temperature It is heated to reflux 5-15 hours；After reaction terminates, cooling Jia Shui, mixture is filtered and dried in vacuum drying chamber, gained is residual Excess crosses silicagel column purifying, obtains compound intermediate I；
    The raw material A withMol ratio be 1: 1.0~3, Pd (OAc)2With the mol ratio of raw material A for 0.001~ 0.04: 1, K3PO4Mol ratio with raw material A is that the amount ratio of 1.0~4.0: 1, DMF dosages and raw material A is 1g:10~30ml；
    (2) Ar is worked as1When being connected with pyridine with C-N keys,
    Equation (2) is answered in first contragradience
    Specifically course of reaction is：
    Weigh raw material A and Ar1- H, dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, sodium tert-butoxide；In inert atmosphere Under, the mixed solution of above-mentioned reactant is reacted 10~24 hours at 95~110 DEG C of reaction temperature, cools down and to filter reaction molten Liquid, filtrate revolving, crosses silicagel column, obtains intermediate compound I；
    The raw material A and Ar1- H mol ratio is 1:1.0~3, Pd2(dba)3Mol ratio with raw material A is 0.006~0.04: 1, the mol ratio of tri-butyl phosphine and raw material A is 0.006~0.04:1, the mol ratio of sodium tert-butoxide and raw material A is 2.0~3.0: 1；
    Second step course of reaction：
    Second step reaction equation
    Under nitrogen atmosphere, weigh intermediate compound I and be dissolved in DMF i.e. DMF, then willAnd vinegar Sour palladium adds, and stirs mixture, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in reaction temperature 120- 10-24 hours are heated to reflux at 150 DEG C；After reaction terminates, cooling Jia Shui, mixture is filtered and done in vacuum drying chamber Dry, gained residue crosses silicagel column purifying, obtains compound intermediate II；
    The intermediate compound I withMol ratio be 1:1.0~3, Pd (OAc)2Mol ratio with intermediate compound I is 0.001~0.04:1, K3PO4Mol ratio with intermediate compound I is 1.0~4.0:The amount ratio of 1, DMF dosage and intermediate compound I is 1g: 10~40ml；
    Three-step reaction process：
    Three-step reaction equation
    Under nitrogen atmosphere, weigh intermediate II and be dissolved in DMF i.e. DMF, then willAnd Palladium adds, and stirs mixture, aqueous potassium phosphate solution is added, by the mixed solution of above-mentioned reactant in reaction temperature 120- 10-24 hours are heated to reflux at 150 DEG C；After reaction terminates, cooling Jia Shui, mixture is filtered and done in vacuum drying chamber Dry, gained residue crosses silicagel column purifying, obtains target compound；
    The intermediate II withMol ratio be 1:1.0~3, Pd (OAc)2With the mol ratio of intermediate II For 0.001~0.04:1, K3PO4Mol ratio with intermediate II is 1.0~4.0:The amount ratio of 1, DMF dosage and intermediate II For 1g:15~50ml.
  4. 4. a kind of organic compound as claimed in claim 1 or 2 using pyridine and benzimidazole as core has for preparation Organic electroluminescence devices.
  5. 5. a kind of organic electroluminescence device, it is characterised in that the organic electroluminescence device includes at least one layer of functional layer Contain the organic compound described in claim 1 or 2 using pyridine and benzimidazole as core.
  6. 6. a kind of organic electroluminescence device, including hole blocking layer/electron transfer layer, it is characterised in that the hole barrier Layer/electron transfer layer contains the organic compound using pyridine and benzimidazole as core described in claim 1 or 2.
  7. 7. a kind of organic electroluminescence device, including CPL layers, it is characterised in that the CPL layers contain described in claim 1 or 2 The organic compound using pyridine and benzimidazole as core.
  8. 8. one kind illumination or display element, it is characterised in that including organic electroluminescence device as claimed in claim 4.
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CN109206422A (en) * 2018-09-27 2019-01-15 武汉尚赛光电科技有限公司 Bipolarity compound and its preparation method and application based on 1,3,4- thiadiazoles
CN109206422B (en) * 2018-09-27 2022-03-18 湖北尚赛光电材料有限公司 Bipolar compound based on 1,3, 4-thiadiazole and preparation method and application thereof
CN110818642A (en) * 2018-12-10 2020-02-21 广州华睿光电材料有限公司 Heterocyclic arylamine compound and application thereof in organic electronic device
CN110818642B (en) * 2018-12-10 2021-09-10 广州华睿光电材料有限公司 Heterocyclic arylamine compound and application thereof in organic electronic device
CN111574504A (en) * 2019-02-19 2020-08-25 江苏三月光电科技有限公司 Organic compound based on aza-benzene and dicarboxyl diamine derivative and application thereof
CN110229145A (en) * 2019-03-28 2019-09-13 江苏三月光电科技有限公司 A kind of organic compound based on pyridine and its application on OLED
CN110669018A (en) * 2019-09-27 2020-01-10 武汉华星光电半导体显示技术有限公司 N-heterocyclic planar optical coupler output material and preparation method thereof
CN111943902B (en) * 2020-08-21 2021-06-08 长春海谱润斯科技股份有限公司 Triarylamine compound and organic light-emitting device thereof
CN111943902A (en) * 2020-08-21 2020-11-17 长春海谱润斯科技有限公司 Triarylamine compound and organic light-emitting device thereof
CN114685427A (en) * 2020-12-28 2022-07-01 常州强力昱镭光电材料有限公司 Quinoline bipyridyl compound and application thereof in organic electroluminescent element
CN114685427B (en) * 2020-12-28 2023-12-22 常州强力昱镭光电材料有限公司 Quinoline bipyridine compound and application thereof in organic electroluminescent element
RU2812517C1 (en) * 2023-11-20 2024-01-30 Федеральное государственное бюджетное учреждение науки Пермский федеральный исследовательский центр Уральского отделения Российской академии наук 2,6-bis-(4-(9h-carbazol-9-yl)phenyl)-4-(4-n,n-diphenylaminophenyl)pyridine exhibiting fluorescent properties and method of its preparation

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