CN110003019A - It is a kind of using equal benzene as the high mobility organic compound of core and its application - Google Patents
It is a kind of using equal benzene as the high mobility organic compound of core and its application Download PDFInfo
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Abstract
The present invention relates to a kind of organic compound for being core with high mobility using equal benzene and its applications, organic compound provided by the invention is using equal benzene as core, connect pyrene branch, organic compound of the present invention has good thermal stability and higher glass transition temperature, there is suitable HOMO energy level simultaneously, using the device of organic compound provided by the invention by structure optimization, the photoelectric properties of OLED device and the service life of OLED device can be effectively promoted.
Description
Technical field
The present invention relates to technical field of semiconductors more particularly to it is a kind of using equal benzene be core with the organic of high mobility
Compound and its application.
Background technique
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology can both be used to make
New display product is made, production novel illumination product is can be used for, is expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is very extensive.
OLED luminescent device including electrode material film layer and is clipped between Different electrodes film layer like the structure of sandwich
Organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together.
OLED luminescent device is as current device, when applying voltage to its two end electrodes, and passes through electric field action organic layer functional material
When positive and negative charge in film layer, positive and negative charge is further compound in electronic barrier layer, i.e. generation OLED electroluminescent.
Proposing high performance research to OLED luminescent device at present includes: the driving voltage for reducing device, the hair for improving device
Light efficiency, the service life for improving device etc..In order to realize OLED device performance continuous promotion, not only need from OLED device
The innovation of part structure and manufacture craft is constantly studied and is innovated with greater need for oled light sulfate ferroelectric functional material, formulates out higher performance
OLED functional material.
In order to make high performance OLED luminescent device, it is desirable that various organic functional materials have good photoelectric properties,
For example, as charge transport materials, it is desirable that have good carrier mobility, high-vitrification conversion temperature etc., as electronics
The material of main part on barrier layer has good bipolarity, HOMO/LUMO energy rank appropriate etc..
Therefore, for the industry application requirement of current OLED device and the different function film layer of OLED device, device
Photoelectric characteristic demand, it is necessary to which selection is more suitable for, the higher OLED functional material of performance or combination of materials, is just able to achieve the height of device
Efficiency, the overall characteristic of long-life and low-voltage.For current OLED shows the actual demand of Lighting Industry, OLED at present
The development of material is also far from enough, lags behind the requirement of panel manufacturing enterprise, as the organic of material enterprise development higher performance
Functional material is particularly important.
Summary of the invention
An object of the present invention, be to provide it is a kind of using equal benzene as the organic compound with high mobility of core,
With good thermal stability and higher glass transition temperature, while there is suitable HOMO energy level, use is provided by the invention
The device of organic compound can effectively promote the photoelectric properties of OLED device and the service life of OLED device by structure optimization.
The technical solution that the present invention solves above-mentioned technical problem is as follows: a kind of to have high mobility using equal benzene as core
Organic compound, shown in the structure of the organic compound such as general formula (1):
In general formula (1), Ar1-Ar5It is expressed as substituted or unsubstituted C6-C30It is aryl, substituted or unsubstituted
C2-C30Heteroaryl;
Described " substituted " to refer at least one hydrogen atom by following substituent group to substitute: adamantyl, cyano, fluorine are former
Son, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthalene, xenyl, pyridyl group, dibenzofuran group, click
Oxazolyl or furyl;
Hetero atom in the heteroaryl is optionally from one of nitrogen, oxygen or sulphur or a variety of.
As a further improvement of the present invention, the Ar1、Ar2、Ar3、Ar4、Ar5It is expressed as general formula (2), general formula
(3), structure shown in general formula (4) or general formula (5):
In general formula (2), X1And X2Independently be expressed as singly-bound, O, S ,-C (R1R2)-or-NR3, and X1And X2It is different
When be expressed as singly-bound;
R1、R2、R3Separately it is expressed as C1-C10Alkyl, C3-C10Naphthenic base, C6-C30Aryl, C2-C30Heteroaryl
Base;
In general formula (2), general formula (3), general formula (4), general formula (5) and general formula (6), Y is expressed as nitrogen-atoms, carbon atom or C-
R4, Y occurs same or different every time, and when with other group bondings, Y is expressed as C;R4It is expressed as hydrogen atom, halogen atom, cyanogen
Base, C1-C20Alkyl, C3-C20Naphthenic base, C1-C20Alkoxy, C6-C30Aryl, C2-C30Heteroaryl.
As a further improvement of the present invention, the Ar1、Ar2、Ar3、Ar4、Ar5At least one be expressed as general formula (2) or
Structure shown in general formula (3).
As a further improvement of the present invention, R1、R2、R3Separately it is expressed as methyl, isopropyl, tert-butyl, Buddha's warrior attendant
Alkyl, phenyl, xenyl, naphthalene, dimethyl fluorenyl, dibenzofuran group, carbazyl, dibenzothiophene, pyridyl group, naphthyridines
Base or carbazole quinoline base;The R4It is expressed as hydrogen atom, fluorine atom, cyano, methoxyl group, methyl, isopropyl, tert-butyl, Buddha's warrior attendant
Alkyl, phenyl, xenyl, naphthalene, dimethyl fluorenyl, diphenyl fluorenyl, Spirofluorene-based, dibenzofuran group, carbazyl, dibenzo
Thienyl, pyridyl group, naphthyridines base or carbazole quinoline base.
As a further improvement of the present invention, the specific structure of the organic compound is expressed as with any in flowering structure
Kind:
Any one of.
The second object of the present invention is to provide the preparation method of above-mentioned organic compound.Preparation method of the invention is simple,
Wide market is suitble to large-scale production.
The technical scheme to solve the above technical problems is that a kind of equal benzene is the preparation of the organic compound of core
Method, the reaction equation that the preparation method is related to are as follows:
It is specific the preparation method is as follows: 250mL there-necked flask, under the atmosphere for being passed through nitrogen, be added intermediate C, raw material D,
Potassium tert-butoxide, Pd2(dba) 3, triphenylphosphine and 150mL solvent toluene are heated to reflux 12 hours, sample contact plate, fully reacting;
Natural cooling, filtering, filtrate revolving cross silicagel column, obtain target product;
Wherein, the molar ratio of the raw material D and intermediate C is (1.0-3.0): 1, mole of potassium tert-butoxide and intermediate C
Than for (1-5): 1, Pd2(dba)3It is (0.01-0.03) with the molar ratio of intermediate C: 1, triphenylphosphine and intermediate C molar ratio
For (0.01-0.03): 1;The dosage of toluene is every 1mol intermediate C (100-150) mL toluene.
The third aspect of the invention is to provide a kind of organic electroluminescence device, including cathode and anode, the cathode
It is provided with organic function layer between anode, has the feature that, above-mentioned organic function layer contains above-mentioned organic compound.
As a further improvement of the present invention, the organic function layer includes hole transmission layer or electronic barrier layer, is had
Such feature, above-mentioned hole transmission layer or electronic barrier layer contain above-mentioned organic compound.
The fifth aspect of the invention is to provide a kind of illumination or display element, has the feature that, including above-mentioned
Organic electroluminescence device.
The present invention is beneficial to be had the technical effect that
1. the structure of organic compound of the invention balances electrons and holes more in the distribution of electronic barrier layer,
Under appropriate HOMO energy level, hole injection and transmission performance are improved;Under suitable lumo energy, and play electronic blocking
Effect, promote combined efficiency of the exciton in electronic barrier layer;Electronic barrier layer materials'use as OLED luminescent device
When, exciton utilization rate and fluorescent radiation efficiency can be effectively improved, the efficiency roll-off under high current density is reduced, reduces device electricity
Pressure, improves current efficiency and the service life of device.
2. organic compound of the invention, in application, by device architecture optimization, can keep high film layer in OLED device
Stability can effectively promote the photoelectric properties of OLED device and the service life of OLED device.Compound of the present invention is in OLED
There is good application effect and industrialization prospect in luminescent device.
Detailed description of the invention
Fig. 1 is the structural schematic diagram that material cited by the present invention is applied to OLED device;Wherein, 1, transparent substrate layer,
2, ito anode layer, 3, hole injection layer, 4, hole transmission layer 5, electronic barrier layer, 6, electronic barrier layer, 7, hole barrier/electricity
Sub- transport layer, 8, electron injecting layer, 9, cathode layer, 10, CPL layers.
Fig. 2 is device prepared by the present invention and the efficiency curve diagram that comparative device measures at different temperatures.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description.
All raw materials are purchased in Fine Chemical Industry Co in following preparation embodiments.
Specifically the preparation method is as follows: 0.01mol raw material A 1 is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml,
Raw material B1, the 0.03mol potassium tert-butoxide of 0.014mol, 1.4 × 10-4mol Pd2(dba)3, 1.3 × 10-4Mol triphenylphosphine,
150ml toluene is heated to 100 DEG C and flows back 12 hours, samples contact plate, fully reacting;Natural cooling, filtering, filtrate revolving cross silicon
Rubber column gel column obtains intermediate C1;HPLC purity 98.6%, yield 86.5%;Elemental analysis structure (molecular formula C36H29N3): theoretical value
C,85.85;H,5.80;N,8.34;Test value: C, 85.87;H,5.81;N,8.34.ESI-MS (m/z) (M+): theoretical value is
503.24 measured value 503.25.
Intermediate C is prepared with the synthetic method of intermediate C1, is directed to raw material A and raw material B specific structure such as 1 institute of table
Show.
Table 1
Prepare embodiment 1: the synthesis of compound 1:
Specifically the preparation method is as follows: the intermediate of 0.01mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml
C1, addition 0.014mol raw material D1,0.03mol potassium tert-butoxide, 1.4 × 10-4mol Pd2(dba)3, 1.3 × 10-4Mol triphenyl
Phosphine, 150ml toluene are heated to 110 DEG C and flow back 12 hours, samples contact plate, fully reacting;Natural cooling, filtering, filtrate revolving,
Silicagel column is crossed, compound 1 is obtained;HPLC purity 99.2%, yield 89.1%;Elemental analysis structure (molecular formula C52H37N3): reason
By value C, 88.73;H,5.30;N,5.97;Test value: C, 88.74;H,5.30;N,5.97.
ESI-MS (m/z) (M+): theoretical value 703.30, measured value 703.32.
The reaction type phase that the reaction type of remaining target compound being related to and the preparation step of compound 1 are related to
Together.
Prepare embodiment 2: the synthesis of compound 3
Prepare embodiment 3: the synthesis of compound 6
Prepare embodiment 4: the synthesis of compound 7
Prepare embodiment 5: the synthesis of compound 10
Prepare embodiment 6: the synthesis of compound 12
Prepare embodiment 7: the synthesis of compound 15
Prepare embodiment 8: the synthesis of compound 22
Prepare embodiment 9: the synthesis of compound 31
Prepare embodiment 10: the synthesis of compound 37
Prepare embodiment 11: the synthesis of compound 51
Prepare embodiment 12: the synthesis of compound 58
Prepare embodiment 13: the synthesis of compound 74
Prepare embodiment 14: the synthesis of compound 87
Prepare embodiment 15: the synthesis of compound 102
The amount of the reactant and catalyst that are related in target compound preparation process, and obtained target compound
Structural characterization is as shown in table 2.
Table 2
Organic compound of the present invention uses in luminescent device, has high glass transition temperature (Tg) and triplet state energy
Grade (T1), suitable HOMO, lumo energy can be used as hole transmission layer and electronic barrier layer materials'use.To the present inventionization
It closes object and carries out hot property, T1 energy level, HOMO energy level, hole mobility and Eg test respectively, the results are shown in Table 3.
Table 3
Note: triplet T1 is tested by the F4600 Fluorescence Spectrometer of Hitachi, and the test condition of material is 2*10- 5The toluene solution of mol/L;By differential scanning calorimetry, (DSC, German Nai Chi company DSC204F1 show that difference is swept to glass transition temperature Tg
Retouch calorimeter) measurement, 10 DEG C/min of heating rate;Highest occupied molecular orbital HOMO energy level is by ionization energy test macro
(IPS-3) it and obtained by ultraviolet specrophotometer (UV) measuring and calculation, tests as atmospheric environment, hole mobility test, by this
Single charge devices are made in invention material, are measured with SCLC method;Eg energy level: (UV inhales the uv-spectrophotometric based on material monofilm
Receive) uplifted side of baseline and the first absorption peak draws tangent line, intersect point value calculating with tangent line and baseline;Meanwhile it can be used
Gaussian16,6-31G (d) base group, B3lyp functional, TD-FDT algorithm optimization geometry carry out HOMO, lumo energy meter
Calculate, Eg=| HOMO-LUMO |.
By upper table data it is found that the compounds of this invention has HOMO energy level appropriate, Eg and higher hole mobility,
It is suitable as hole transmission layer and electronic blocking layer material;Meanwhile the compounds of this invention thermal stability with higher, so that answering
It is got a promotion with the OLED device service life of the compounds of this invention.
Make in the devices below by way of device embodiments 1~37 and comparative example 1 compound that the present invention will be described in detail synthesizes
For the application effect of hole transmission layer and electronic barrier layer.Device embodiments 2~37, device comparative example 1 and 1 phase of device embodiments
Than the manufacture craft of the device is identical, and uses identical baseplate material and electrode material, electrode material
Film thickness is also consistent, except that the material of 2~17 hole-transporting layer of device embodiments is changed;Device is implemented
The electronic blocking layer material of device is converted in example 18~37, the structure of each embodiment obtained device is as shown in table 4.
Device embodiments 1
As shown in Figure 1, a kind of preparation method of electroluminescent device, includes the following steps:
Transparent substrate layer 1 is transparent PI film, washs to ito anode layer 2 (film thickness 150nm), i.e., successively carries out alkali
Washing, pure water, drying, then ultraviolet-ozone washing is carried out to remove the organic residue on the transparent surface ITO.Carry out
On ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, HAT-CN that film thickness is 10nm is deposited as hole
Implanted layer 3 uses.Then the compound 1 that 60nm thickness is deposited is used as hole transmission layer.Then the EB-1 of vapor deposition 20nm thickness makees
For electronic barrier layer.Then make OLED luminescent device luminescent layer 6, structure include the used GH-1 of OLED luminescent layer 6,
GH-2 is 10% weight ratio as dopant material, dopant material doping ratio as material of main part, GD-1, and luminescent layer film thickness is
40nm.After above-mentioned luminescent layer 6, continuation vacuum evaporation electron transport layer materials are ET-1 and Liq.The vacuum evaporation of the material
Film thickness is 30nm, this layer is hole barrier/electron transfer layer 7.On hole barrier/electron transfer layer 7, filled by vacuum evaporation
It sets, lithium fluoride (LiF) layer that production film thickness is 1nm, this layer is electron injecting layer 8.On electron injecting layer 8, steamed by vacuum
Plating appts, the Mg:Ag electrode layer that production film thickness is 15nm, this layer are the use of cathode layer 9.On cathode layer 9, vacuum evaporation 70nm
CP-1, as CPL layer 10.
The structure of related current material is as follows:
After completing OLED luminescent device as described above, anode and cathode is connected with well known driving circuit, is surveyed
The service life of the current efficiency of metering device, luminescent spectrum and device.The test result of obtained device is shown in Table 5 and shows.
Table 4
Table 5
Illustrate: device detection performance is using comparative example 1 as reference;Current efficiency is in 10mA/cm2Under the conditions of measure;Longevity
Life test macro is Japan System Engineer's Co., and the OLED device service life of the model EAS-62C of LTD exploitation surveys
Try instrument.
Table 5 the result shows that the compounds of this invention as hole transmission layer and electronic blocking layer material can be applied to OLED hair
Optical device production, and compared with comparative example 1, either efficiency or service life obtain larger change than known OLED material,
Especially the driving service life of device obtains biggish promotion.
Work limitation rate is also more stable at low temperature for the OLED device of further material preparation of the present invention, by device reality
It applies example 1,8,18 and device comparative example 1 and carries out efficiency test in -10~80 DEG C of sections, acquired results are as shown in table 6 and Fig. 2.
Table 6
From the data of table 6 it is found that embodiment 1,8,18 is material of the present invention and device architecture and device that known materials are arranged in pairs or groups
Part comparative example 1 is compared, and not only Efficiency at Low Temperature is high, but also in temperature elevation process, efficiency is steadily increased.
From the point of view of above data application, the compounds of this invention is sent out as hole transmission layer or electronic blocking layer material in OLED
There is good application effect in optical device, there is good industrialization prospect.
Claims (7)
1. a kind of using equal benzene as the organic compound with high mobility of core, which is characterized in that the organic compound
Shown in structure such as general formula (1):
In general formula (1), Ar1-Ar5It is expressed as substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30
Heteroaryl;
It is described " substituted " to refer at least one hydrogen atom by following substituent group to substitute: adamantyl, cyano, fluorine atom, first
Base, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthalene, xenyl, pyridyl group, dibenzofuran group, carbazyl or
Furyl;
Hetero atom in the heteroaryl is optionally from one of nitrogen, oxygen or sulphur or a variety of.
2. organic compound according to claim 1, which is characterized in that the Ar1、Ar2、Ar3、Ar4、Ar5It respectively indicates
For structure shown in general formula (2), general formula (3), general formula (4) or general formula (5):
In general formula (2), X1And X2Independently be expressed as singly-bound, O, S ,-C (R1R2)-or-NR3, and X1And X2It does not indicate simultaneously
For singly-bound;
R1、R2、R3Separately it is expressed as C1-C10Alkyl, C3-C10Naphthenic base, C6-C30Aryl, C2-C30Heteroaryl;
In general formula (2), general formula (3), general formula (4), general formula (5) and general formula (6), Y is expressed as nitrogen-atoms, carbon atom or C-R4, Y is every
Secondary appearance is same or different, and when with other group bondings, Y is expressed as C;R4It is expressed as hydrogen atom, halogen atom, cyano, C1-
C20Alkyl, C3-C20Naphthenic base, C1-C20Alkoxy, C6-C30Aryl, C2-C30Heteroaryl.
3. organic compound according to claim 1, which is characterized in that the Ar1、Ar2、Ar3、Ar4、Ar5At least one
It is a to be expressed as structure shown in general formula (2) or general formula (3).
4. organic compound according to claim 1 or 2, which is characterized in that the R1、R2、R3Separately it is expressed as
Methyl, isopropyl, tert-butyl, adamantyl, phenyl, xenyl, naphthalene, dimethyl fluorenyl, dibenzofuran group, carbazyl,
Dibenzothiophene, pyridyl group, naphthyridines base or carbazole quinoline base;The R4Be expressed as hydrogen atom, fluorine atom, cyano, methoxyl group,
Methyl, isopropyl, tert-butyl, adamantyl, phenyl, xenyl, naphthalene, dimethyl fluorenyl, diphenyl fluorenyl, it is Spirofluorene-based, two
Benzofuranyl, carbazyl, dibenzothiophene, pyridyl group, naphthyridines base or carbazole quinoline base.
5. organic compound according to claim 1, which is characterized in that the specific structure of the organic compound is expressed as
With any one of flowering structure:
Any one of.
6. a kind of organic electroluminescence device, including cathode and anode, are provided with organic function layer between the cathode and anode,
It is characterized in that, the organic function layer includes the described in any item organic compounds of claim 1-5.
7. a kind of organic electroluminescence device according to claim 5, the organic function layer include electronic barrier layer or
Hole transmission layer, which is characterized in that the electronic barrier layer or hole transmission layer contain that claim 1-5 is described in any item to be had
Machine compound.
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