CN106467486A - A kind of organic compound containing dimethylanthracene and its application - Google Patents

A kind of organic compound containing dimethylanthracene and its application Download PDF

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CN106467486A
CN106467486A CN201610738441.0A CN201610738441A CN106467486A CN 106467486 A CN106467486 A CN 106467486A CN 201610738441 A CN201610738441 A CN 201610738441A CN 106467486 A CN106467486 A CN 106467486A
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organic compound
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CN106467486B (en
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张兆超
李崇
叶中华
张小庆
王立春
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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 invention discloses a kind of organic compound containing dimethylanthracene and its application on organic electroluminescence device, shown in the structural formula formula such as formula (1) of this organic compound.The compounds of this invention has higher vitrification point and molecule heat stability, suitable HOMO and lumo energy, higher Eg, is optimized by device architecture, can effectively lift the photoelectric properties of OLED and the life-span of OLED.

Description

A kind of organic compound containing dimethylanthracene and its application
Technical field
The present invention relates to organic photoelectrical material technical field, especially relate to one kind containing bone centered on dimethylanthracene structure The compound-material of frame and its application in OLED field.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to make Make new display product it is also possible to 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 device just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute OLED luminescent device together. As current device, when the two end electrodes applied voltage to OLED luminescent device, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is compound in luminescent layer further, that is, produce OLED electroluminescent.
Currently, in smart mobile phone, the field such as panel computer obtains application to OLED Display Technique, further also will be to electricity Depending on etc. the extension of large scale application, but, require to compare with the products application of reality, the luminous efficiency of OLED, use The performances such as life-span also need to be lifted further.
High performance research is carried for OLED luminescent device include：Reduce the driving voltage of device, improve the luminous of device Efficiency, improves service life of device etc..In order to realize the continuous lifting of the performance of OLED, not only need from OLED Structure and the innovation of processing technology, constantly study with greater need for oled light sulfate ferroelectric functional material and innovate, formulate out higher performance OLED Functional material.
The oled light sulfate ferroelectric functional material being applied to OLED can be divided into two big class from purposes, i.e. electric charge injection transmission Material and luminescent material, further, also can inject charge into transmission material and be divided into electron injection transmission material, electronic blocking material Luminescent material can also be divided into main body luminescent material and dopant material by material, hole injection transmission material and hole barrier materials.
In order to make high performance OLED luminescent device it is desirable to various organic functional material possesses good photoelectric characteristic, Such as, as charge transport materials it is desirable to have good carrier mobility, high-vitrification conversion temperature etc., as luminous The material of main part of layer requires material to have good bipolarity, suitable HOMO/LUMO energy rank etc..
The oled light sulfate ferroelectric functional material film layer constituting OLED at least includes the above structure of two-layer, application in industry OLED structure, then include hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography Multiple film layer such as defeated layer, electron injecting layer is that is to say, that the photoelectric functional material being applied to OLED includes at least hole note Enter material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form have rich and many The feature of sample.In addition, for the OLED of different structure is arranged in pairs or groups, the photoelectric functional material that used has stronger Selectivity, performance in different structure device for the identical material is it is also possible to completely totally different.
Therefore, for the industry application requirement of current OLED, and the difference in functionality film layer of OLED, device Photoelectric characteristic demand, it is necessary to select to be more suitable for, has high performance OLED functional material or combination of materials, just enables device The overall characteristic of high efficiency, long-life and low-voltage.For the actual demand that current OLED shows Lighting Industry, current OLED The development of material is also far from enough, lags behind the requirement of panel manufacturing enterprise, organic as material enterprise development higher performance Functional material is particularly important.
Content of the invention
The problems referred to above existing for prior art, the applicant provides a kind of organic compound containing dimethylanthracene And its apply on organic electroluminescence device.The compounds of this invention contains dimethylanthracene structure, has higher vitrification temperature Degree and molecule heat stability, suitable HOMO and lumo energy, higher Eg, optimized by device architecture, can effectively lift OLED The photoelectric properties of device and the life-span of OLED.
Technical scheme is as follows：
The applicant provides a kind of organic compound containing dimethylanthracene, the structural formula formula such as formula of this compound (1) shown in：
Wherein, Ar1、Ar2It is expressed as phenyl, xenyl or naphthyl；
R1、R2Independently be expressed as structure shown in formula (2)；R1With R2Can be identical or different；R1Also may indicate that For hydrogen atom；
In formula (2), R3、R4Independently be expressed as hydrogen atom, formula (3) or structure shown in formula (4)；
In formula (3), a is selected fromX1、X2、X3Independently to be expressed as oxygen former Son, sulphur atom, selenium atom, C1-10The alkylidene that the alkylidene of straight or branched alkyl replacement, aryl replace, alkyl or aryl take One of the tertiary amine groups in generation；
Formula (3) or formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3-CL’4Key is connected with formula (2).
Preferably, described R1、R2Being expressed as independently：
In any one.
Preferably, the concrete structure formula of the described organic compound containing dimethylanthracene is：
In any one.
The applicant additionally provides a kind of preparation method of described organic compound, works as R1When being expressed as hydrogen atom, this system Reaction equation in Preparation Method is：
Described preparation method is with Br-Ar2- MgBr is raw material, by grignard reaction, prepared Grignard reagent, then and diformazan Base anthrone reaction, generates the tertiary alcohol；The subsequently tertiary alcohol and H-Ar1Reacted by friedel-craft, a bromo compound, Ran Houhe are obtainedIt is coupled by C-N and described organic compound is obtained.
The applicant additionally provides the preparation method of another kind of described organic compound it is characterised in that working as R1It is expressed as During the structure of formula (2), the reaction equation in this preparation method is：
Described preparation method is with Br-Ar2- MgBr is raw material, by grignard reaction, prepared Grignard reagent, then and diformazan Base anthrone reaction, generates the tertiary alcohol, the tertiary alcohol and H-Ar1- Br is reacted by friedel-craft, and two bromo compounds, Ran Houhe are obtainedIt is coupled by C-N and described organic compound is obtained.
The applicant additionally provides a kind of organic electroluminescence device, and described organic electroluminescence device includes at least one of which Functional layer contains the described organic compound containing dimethylanthracene.
Beneficial the having technical effect that of the present invention：
The compounds of this invention with dimethylanthracene as parent nucleus, connected symmetrical dendrimer or asymmetrical rigid radical, the knot of saboteur Crystalline substance, it is to avoid intermolecular aggregation, has high vitrification point, and material, when OLED is applied, can keep high Membranous layer stability, improves OLED service life.
The compounds of this invention structure makes electronics and hole more balance in the distribution of luminescent layer, in appropriate HOMO energy level Under, improve hole injection/transmission performance；Under suitable lumo energy, serve the effect of electronic blocking again, lift exciton Combined efficiency in luminescent layer；As OLED luminescent device light emitting functional layer materials'use when, aryl replace dimethyl The side chain that anthracene is arranged in pairs or groups in the scope of the invention can effectively improve exciton utilization rate and high fluorescent radiation efficiency, reduces under high current density Efficiency roll-off, reduce device voltage, improve the current efficiency of device and life-span.
The special construction of compound of the present invention designs so that material also has while having high decomposition temperature Low sublimation temperature or vacuum evaporation temperature, have higher temperature difference window between sublimation temperature or evaporation temperature and decomposition temperature Mouth, so that material has higher operation controllability in commercial Application, is applied beneficial to material volume production.
Compound of the present invention has good application effect in OLED luminescent device, before having good industrialization Scape.
Brief description
Materials application cited by the present invention for the Fig. 1 is in the structural representation of OLED；
Wherein, 1 is transparent substrate layer, and 2 is ito anode layer, and 3 is hole injection layer, and 4 is hole transport/electronic barrier layer, 5 is luminescent layer, and 6 is electric transmission/hole blocking layer, and 7 is electron injecting layer, and 8 is negative electrode reflection electrode layer.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1：The synthesis of intermediate A 1：
Synthetic route：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, add 11.8g Isosorbide-5-Nitrae-dibromobenzene (0.05mol) and 1.33gMg powder (0.055mol), 60ml oxolane, it is heated to reflux 4 hours, reaction completely, generates grignard reagent；
11.1g10,10- dimethyl anthrone (0.05mol) are dissolved in 50ml oxolane, the above-mentioned grignard reagent of Deca, and 60 DEG C reaction 24 hours, generate a large amount of white precipitates, be eventually adding saturation NHCl4Form salt is converted into alcohol；After completion of the reaction, second Ether extracts, and revolving, petroleum ether are dried：Dichloromethane mixed solvent (3:2) silica column purification, obtains the solid tertiary alcohol of yellowish (yield is 88%)；Identify this compound, molecular formula C using DEI-MS22H19BrO, detected value [M+1]+=379.03, calculate Value 378.06；
By 1:2 when measuring the above-mentioned tertiary alcohol of 15.2g (0.04mol) and 12.5g bromobenzene (0.08mol) is dissolved in 100ml dichloromethane In alkane, Deca 8ml boron trifluoride etherate at ambient temperature, reacts 30 minutes, adds 20ml ethanol and 20ml water Reaction is quenched, with dichloromethane (20ml*3) extraction, revolving, petroleum ether silica column purification is dried, uses ethanol：Dichloromethane is tied again Crystalline substance, yield is 75%；Identify this compound, molecular formula C using DEI-MS28H22Br2, detected value [M+1]+=516.87, meter Calculation value 516.01；
Embodiment 2：The synthesis of intermediate A 2：
Synthetic route：
Prepare intermediate A 2 by the synthetic method of the intermediate A 1 in embodiment 1, difference is to use 1,1 '-biphenyl replaces Compound bromobenzene；
Identify this compound, molecular formula C using DEI-MS34H27Br, detected value [M+1]+=514.85, value of calculation 514.13.
Embodiment 3：The synthesis of intermediate A 3：
Synthetic route：
Prepare intermediate A 3 by the synthetic method of the intermediate A 1 in embodiment 1, difference is to use in three-step reaction Benzene replaces bromobenzene；
Identify this compound, molecular formula C using DEI-MS28H23Br, detected value [M+1]+=438.10, value of calculation 438.87.
Embodiment 4：The synthesis of intermediate A 4：
Synthetic route：
Prepare intermediate A 4 by the synthetic method of the intermediate A 1 in embodiment 1, difference is to use in first step reaction 1,3- dibromobenzene replaces 1,4- dibromobenzene；
Identify this compound, molecular formula C using DEI-MS28H23Br, detected value [M+1]+=438.10, value of calculation 438.84.
Embodiment 5：The synthesis of intermediate A 5：
Synthetic route：
Prepare intermediate A 5 by the synthetic method of the intermediate A 1 in embodiment 1, difference is to use in first step reaction 1,3- dibromine naphthalene replaces 1,4- dibromobenzene；
Identify this compound, molecular formula C using DEI-MS32H25Br, detected value [M+1]+=488.93, value of calculation 488.11.
Embodiment 6：The synthesis of compound 1：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol intermediate A 1,0.024mol intermediate B 1, 0.04mol sodium tert-butoxide, 1 × 10-4molpd2(dba)3, 1 × 10-4Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 little When, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.5%, yield 65.2%；
Elementary analysiss structure (molecular formula C60H42N2)：Theoretical value C, 91.11；H,5.35；N,3.54；Test value：C, 91.09；H,5.33；N,3.58.
HPLC-MS：Material molecule amount is 790.99, surveys molecular weight 791.25.
Embodiment 7：The synthesis of compound 3：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol intermediate A 2,0.012mol intermediate B 2, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.3%, yield 72.5%；
Elementary analysiss structure (molecular formula C54H39N)：Theoretical value C, 92.40；H,5.60；N,2.00；Test value：C, 92.37；H,5.61；N,2.02.
HPLC-MS：Material molecule amount is 701.89, surveys molecular weight 702.21.
Embodiment 8：The synthesis of compound 10：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol intermediate A 3,0.012mol intermediate C1, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.4%, yield 71.9%；
Elementary analysiss structure (molecular formula C52H38N2)：Theoretical value C, 90.40；H,5.54；N,4.05；Test value：C, 90.46；H,5.52；N,4.02.
HPLC-MS：Material molecule amount is 690.87, surveys molecular weight 691.18.
Embodiment 9：The synthesis of compound 11：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate C2；
Elementary analysiss structure (molecular formula C46H33NO)：Theoretical value C, 89.73；H,5.40；N,2.27；O,2.60；Test Value：C,89.73；H,5.42；N,2.26；O,2.59.
HPLC-MS：Material molecule amount is 615.76, surveys molecular weight 616.02.
Embodiment 10：The synthesis of compound 14：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate D1；
Elementary analysiss structure (molecular formula C50H35NO)：Theoretical value C, 90.19；H,5.30；N,2.10；O,2.40；Test Value：C,90.16；H,5.32；N,2.11；O,2.41.
HPLC-MS：Material molecule amount is 665.82, surveys molecular weight 666.03.
Embodiment 11：The synthesis of compound 18：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate C3；
Elementary analysiss structure (molecular formula C52H38N2)：Theoretical value C, 90.40；H,5.54；N,4.05；Test value：C, 90.16；H,5.32；N,2.11.
HPLC-MS：Material molecule amount is 665.82, surveys molecular weight 666.03.
Embodiment 12：The synthesis of compound 31：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate E 1；
Elementary analysiss structure (molecular formula C58H47N)：Theoretical value C, 91.90；H,6.25；N,1.85；Test value：C, 91.90；H,6.24；N,1.86.
HPLC-MS：Material molecule amount is 758.00, surveys molecular weight 758.32.
Embodiment 13：The synthesis of compound 40：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate E 2；
Elementary analysiss structure (molecular formula C58H47N)：Theoretical value C, 91.90；H,6.25；N,1.85；Test value：C, 91.89；H,6.26；N,1.85.
HPLC-MS：Material molecule amount is 758.00, surveys molecular weight 758.31.
Embodiment 14：The synthesis of compound 41：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol intermediate A 5,0.012mol intermediate E 1, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 99.1%, yield 62.8%；
Elementary analysiss structure (molecular formula C59H43NS)：Theoretical value C, 88.80；H,5.43；N,1.76；S,4.02；Test Value：C,88.82；H,5.42；N,1.75；S,4.01.
HPLC-MS：Material molecule amount is 798.04, surveys molecular weight 798.39.
Embodiment 15：The synthesis of compound 44：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate E 4；
Elementary analysiss structure (molecular formula C52H35NO2)：Theoretical value C, 88.48；H,5.00；N,1.98；O,4.53；Test Value：C,88.49；H,5.01；N,1.99；O,4.51.
HPLC-MS：Material molecule amount is 705.84, surveys molecular weight 706.05.
Embodiment 16：The synthesis of compound 51：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate E 5；
Elementary analysiss structure (molecular formula C58H47N)：Theoretical value C, 91.90；H,6.25；N,1.85；Test value：C, 91.90；H,6.26；N,1.84.
HPLC-MS：Material molecule amount is 758.00, surveys molecular weight 758.39.
Embodiment 17：The synthesis of compound 54：
Synthetic route：
In the there-necked flask of 250ml, under logical nitrogen protection, addition 0.01mol intermediate A 4,0.012mol intermediate E 6, 0.03mol sodium tert-butoxide, 5 × 10-5mol pd2(dba)3, 5 × 10-5Mol tri-tert phosphorus, 150ml toluene, it is heated to reflux 24 Hour, sample point plate, reaction is completely；Natural cooling, filters, filtrate revolving, column chromatography obtains target product, HPLC purity 98.8%, yield 65.6%；
Elementary analysiss structure (molecular formula C53H38N2Se)：Theoretical value C, 81.42；H,4.90；N,3.58；Se,10.10；Survey Examination value：C,81.41；H,4.89；N,3.59；Se,10.11.
HPLC-MS：Material molecule amount is 781.84, surveys molecular weight 782.03.
Embodiment 18：The synthesis of compound 66：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate F1 generation；
Elementary analysiss structure (molecular formula C49H39NO)：Theoretical value C, 89.46；H,5.98；N,2.13；O,2.43；Test Value：C,89.47；H,5.99；N,2.12；O,2.42.
HPLC-MS：Material molecule amount is 657.84, surveys molecular weight 658.04.
Embodiment 19：The synthesis of compound 70：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate F2；
Elementary analysiss structure (molecular formula C55H44N2)：Theoretical value C, 90.13；H,6.05；N,3.82；Test value：C, 90.15；H,6.04；N,3.81.
HPLC-MS：Material molecule amount is 732.95, surveys molecular weight 733.21.
Embodiment 20：The synthesis of compound 84：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate F3；
Elementary analysiss structure (molecular formula C52H38N2O)：Theoretical value C, 88.36；H,5.42；N,3.96；O,2.26；Test Value：C,88.37；H,5.43；N,3.95；O,2.25.
HPLC-MS：Material molecule amount is 706.87, surveys molecular weight 707.05.
Embodiment 21：The synthesis of compound 86：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate F4；
Elementary analysiss structure (molecular formula C49H39NO)：Theoretical value C, 89.46；H,5.98；N,2.13；O,2.43；Test Value：C,89.46；H,5.97；N,2.14；O,2.43.
HPLC-MS：Material molecule amount is 657.84, surveys molecular weight 658.07.
Embodiment 22：The synthesis of compound 91：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate G1；
Elementary analysiss structure (molecular formula C58H47NO2)：Theoretical value C, 88.18；H,6.00；N,1.77；O,4.05；Test Value：C,88.23；H,5.97；N,1.76；O,4.04.
HPLC-MS：Material molecule amount is 790.00, surveys molecular weight 790.28.
Embodiment 23：The synthesis of compound 96：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate G2；
Elementary analysiss structure (molecular formula C61H46N2O)：Theoretical value C, 89.02；H,5.63；N,3.40；O,1.94；Test Value：C,89.02；H,5.62；N,3.41；O,1.95.
HPLC-MS：Material molecule amount is 823.03, surveys molecular weight 823.35.
Embodiment 24：The synthesis of compound 104：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate H1；
Elementary analysiss structure (molecular formula C54H40N2)：Theoretical value C, 90.47；H,5.62；N,3.91；Test value：C, 90.49；H,5.61；N,3.90.
HPLC-MS：Material molecule amount is 716.91, surveys molecular weight 717.22.
Embodiment 25：The synthesis of compound 112：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate G3；
Elementary analysiss structure (molecular formula C70H57N3)：Theoretical value C, 89.42；H,6.11；N,4.47；Test value：C, 89.45；H,6.10；N,4.45.
HPLC-MS：Material molecule amount is 940.22, surveys molecular weight 940.56.
Embodiment 26：The synthesis of compound 119：
Synthetic route：
By the synthetic method preparation of compound 10 in embodiment 8, difference is to replace intermediate C1 with intermediate G4；
Elementary analysiss structure (molecular formula C67H51N3O)：Theoretical value C, 88.03；H,5.62；N,4.60；O,1.75；Test Value：C,88.04；H,5.63；N,4.59O,1.74.
HPLC-MS：Material molecule amount is 914.14, surveys molecular weight 914.53.
The compounds of this invention uses in luminescent device, can be as hole transport/electronic blocking layer material it is also possible to make For luminescent layer Subjective and Objective materials'use.The compounds of this invention has high operability and practicality, major embodiment in application For having high glass transition temperature, low sublimation temperature, high decomposition temperature and film forming stability.
Hot property, HOMO energy level are carried out respectively to the compounds of this invention 10, compound 55, compound 66, current material CBP Test, testing result is as shown in table 1.
Table 1
Note：Vitrification point Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimetry Instrument) measure, 10 DEG C/min of heating rate；Evaporation temperature is using SUNIC evaporated device, vacuum ＜ 1E-5Pa, material rate ForWhen evaporation temperature；Thermal weight loss temperature Td is in nitrogen atmosphere weightless 1% temperature, in Japanese Shimadzu Corporation It is measured on TGA-50H thermogravimetric analyzer, nitrogen flow is 20mL/min；Film forming stability refers to, using SUNIC evaporator Platform, is deposited with to glass substrate 100nm thickness thin film material, envelope in glove box environment (water oxygen content equal ＜ 1PPm) Dress, after encapsulation, glass sample under the conditions of double 80 (humidity 80%, 80 DEG C of temperature) places test 240 hours, uses micro- sem observation The crystal property of sample film；Highest occupied molecular orbital HOMO energy level and minimum occupied molecular orbital lumo energy are by photoelectron Transmitting spectrometer (AC-2 type PESA) test, tests as atmospheric environment.
From upper table data, the compounds of this invention has adjustable HOMO energy level, is suitable as difference in functionality layer material Use；Low evaporation temperature can make material in commercial Application, reduces heat radiation to Fine-mask influence of crust deformation in evaporation board, Improve OLED PPI grade, improve producing line yield；High film forming stability energy, ensure that material is being applied to OLED device During use after part, keep film morphology, do not formed local-crystalized, cause device electrode short circuit, improving OLED makes Use the life-span.
The OLED material describing present invention synthesis in detail below by way of device embodiments 1～10 and comparative example 1 is in the devices Application effect.The making work of device embodiments 2～10 of the present invention, comparative example 1 described device compared with device embodiments 1 Skill is identical, and employed identical baseplate material and electrode material, and the thickness of electrode material is also consistent, and institute is not Be that the material of main part of luminescent layer 5 in 2～9 pairs of devices of device converts；Device 10 uses material of the present invention to make For hole transport/electronic barrier layer application.The performance test results of each embodiment obtained device are as shown in table 2.
Device embodiments 1
A kind of electroluminescent device, its preparation process includes：
A) the ito anode layer 2 on cleaning transparent substrate layer 1, deionized water, acetone, EtOH Sonicate cleaning each 15 respectively Minute, then process 2 minutes in plasma cleaner；
B) on ito anode layer 2, hole injection layer material HAT-CN is deposited with by vacuum evaporation mode, thickness is 10nm, This layer is as hole injection layer 3；
C) on hole injection layer 3, hole mobile material NPB is deposited with by vacuum evaporation mode, thickness is 80nm, this layer For hole transmission layer/electronic barrier layer 4；
D) it is deposited with luminescent layer 5 on hole transport/electronic barrier layer 4, the compounds of this invention 7 is used as main body Material, Ir (ppy)3As dopant material, material doped mass ratio is 10%, and thickness is 30nm；
E) on luminescent layer 5, electron transport material TPBI is deposited with by vacuum evaporation mode, thickness is 40nm, this layer 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 is 1nm, and this layer is electricity Sub- implanted layer 7；
G) on electron injecting layer 7, vacuum evaporation negative electrode Mg:Ag/Ag layer, Mg:Ag doping ratio is 9:1, thickness 15nm, Ag thickness 3nm, this layer is negative electrode reflection electrode layer 8；
Complete the making of electroluminescent device according to above-mentioned steps after, the current efficiency of measurement device and life-span, its result It is shown in Table 2.
The molecular machinery formula of associated materials is as follows：
Device embodiments 2
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 10, dopant material is Ir (ppy)3, doping mass ratio is 10%, the detection data of gained electroluminescent device It is shown in Table 2.
Device embodiments 3
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 13, dopant material is Ir (ppy)3, doping mass ratio is 10%, the detection data of gained electroluminescent device It is shown in Table 2.
Device embodiments 4
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 10 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 5
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 66 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 6
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 72 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 7
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 81 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 8
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 86 and compound GHN, dopant material Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, institute The detection data obtaining electroluminescent device is shown in Table 2.
Device embodiments 9
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into The compounds of this invention 91 and compound GHN, dopant material is Ir (ppy)3, the blending mass ratio of three kinds of materials is 60:30:10, The detection data of gained electroluminescent device is shown in Table 2.
Device embodiments 10
The present embodiment is with the difference of device embodiments 1：Hole transport/the electronic barrier layer of electroluminescent device 4 material is changed into the compounds of this invention 40, and the material of main part of luminescent layer 5 is known compound CBP, and dopant material is Ir (ppy)3, doping mass ratio is 10%, and the detection data of gained electroluminescent device is shown in Table 2.
Device comparative example 1
The present embodiment is with the difference of device embodiments 1：The luminescent layer material of main part of electroluminescent device is changed into Known compound CBP, the detection data of gained electroluminescent device is shown in Table 2.
Table 2
Note：Using device comparative example 1 as reference, comparative example 1 device property indices are set to 1.0 to device detection performance. The current efficiency of comparative example 1 is 28cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.33,0.63)；The LT95 longevity under 5000 brightness Life decays to 2.5Hr.
Can be seen that the machine compound containing dimethylanthracene structure of the present invention can be applicable to OLED and sends out by the result of table 2 Optical device makes, and compared with comparative example, either efficiency or life-span all ratio known OLED material larger changes of acquisition, special It is not the larger lifting of the life time decay acquisition of device.
To sum up, the foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all essences in the present invention Within god and principle, any modification, equivalent substitution and improvement made etc., should be included within the scope of the present invention.

Claims (6)

1. a kind of organic compound containing dimethylanthracene is it is characterised in that the structural formula formula such as formula (1) of described compound Shown：
Wherein, Ar1、Ar2It is expressed as phenyl, xenyl or naphthyl；
R1、R2Independently be expressed as structure shown in formula (2)；R1With R2Can be identical or different；R1It is also denoted as hydrogen Atom；
In formula (2), R3、R4Independently be expressed as hydrogen atom, formula (3) or structure shown in formula (4)；
In formula (3), a is selected fromX1、X2、X3Independently be expressed as oxygen atom, sulfur Atom, selenium atom, C1-10The alkylidene that the alkylidene of straight or branched alkyl replacement, aryl replace, alkyl or aryl replace One of tertiary amine groups；
Formula (3) or formula (4) pass through CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL‘1-CL’2Key, CL‘2-CL’3Key or CL‘3- CL’4Key is connected with formula (2).
2. organic compound according to claim 1 is it is characterised in that described R1、R2Being expressed as independently：
In any one.
3. organic compound according to claim 1 is it is characterised in that the described organic compound containing dimethylanthracene Concrete structure formula is：
In any one.
4. a kind of preparation method of organic compound described in claim 1 is it is characterised in that work as R1When being expressed as hydrogen atom, this system Reaction equation in Preparation Method is：
Described preparation method is with Br-Ar2- MgBr is raw material, by grignard reaction, prepared Grignard reagent, and then anti-with dimethyl anthrone Should, generate the tertiary alcohol；The subsequently tertiary alcohol and H-Ar1Reacted by friedel-craft, a bromo compound, Ran Houhe are obtained It is coupled by C-N and described organic compound is obtained.
5. a kind of preparation method of organic compound described in claim 1 is it is characterised in that work as R1It is expressed as the structure of formula (2) When, the reaction equation in this preparation method is：
Described preparation method is with Br-Ar2- MgBr is raw material, by grignard reaction, prepared Grignard reagent, and then anti-with dimethyl anthrone Should, generate the tertiary alcohol, the tertiary alcohol and H-Ar1- Br is reacted by friedel-craft, and two bromo compounds, Ran Houhe are obtained It is coupled by C-N and described organic compound is obtained.
6. a kind of organic electroluminescence device is it is characterised in that described organic electroluminescence device includes at least one of which functional layer Containing the organic compound containing dimethylanthracene described in any one of Claims 1 to 5.
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Cited By (9)

* Cited by examiner, † Cited by third party
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WO2018080126A1 (en) * 2016-10-24 2018-05-03 주식회사 엘지화학 Heterocyclic compound and organic light-emitting device comprising same
CN109415374A (en) * 2016-10-24 2019-03-01 株式会社Lg化学 Heterocyclic compound and organic illuminating element comprising it
CN107188873A (en) * 2017-06-12 2017-09-22 长春海谱润斯科技有限公司 A kind of phosphorescent light body material and organic luminescent device containing spirane structure
CN107216279A (en) * 2017-06-12 2017-09-29 江苏三月光电科技有限公司 A kind of compound as core using dibenzocycloheptene and its application on organic electroluminescence device
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CN107353290A (en) * 2017-07-05 2017-11-17 江苏三月光电科技有限公司 It is a kind of using dimethyl anthrone as the compound of core and its application on organic electroluminescence device
CN107513034A (en) * 2017-09-29 2017-12-26 江苏三月光电科技有限公司 A kind of dimethylanthracene class organic compound and its application
CN107602470A (en) * 2017-09-29 2018-01-19 江苏三月光电科技有限公司 A kind of dimethylanthracene class organic compound and its application in OLED
CN107686487A (en) * 2017-09-29 2018-02-13 江苏三月光电科技有限公司 A kind of dimethylanthracene class organic compound and its application on organic electroluminescence device
CN107513034B (en) * 2017-09-29 2020-11-03 中节能万润股份有限公司 Dimethyl anthracene organic compound and application thereof
US11124521B2 (en) 2018-04-11 2021-09-21 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same

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