CN109928887A - A kind of organic compound and its application with high mobility - Google Patents

A kind of organic compound and its application with high mobility Download PDF

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CN109928887A
CN109928887A CN201910279212.0A CN201910279212A CN109928887A CN 109928887 A CN109928887 A CN 109928887A CN 201910279212 A CN201910279212 A CN 201910279212A CN 109928887 A CN109928887 A CN 109928887A
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梁丽
王芳
谢丹丹
吴秀芹
张兆超
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Priority to CN201910536481.0A priority patent/CN110156612B/en
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Abstract

Invention is related to a kind of organic compound with high mobility and its application, belongs to technical field of semiconductors.Organic compound provided by the invention, shown in structure such as general formula (1),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

A kind of organic compound and its application with high mobility
Technical field
The present invention relates to technical field of semiconductors more particularly to a kind of organic compound with high mobility and its answer With.
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 is to provide a kind of organic compound with high mobility, steady with good heat Qualitative and higher glass transition temperature, while there is suitable HOMO energy level, using the device of organic compound provided by the invention Part 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 organic compound with high mobility, 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；
X is expressed as-O- ,-S- ,-C (R1)(R2) or-N (R3One of)-；
Z is expressed as C, N or C-R4；
R4It is expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, C1-C10Alkyl, C3-C10Cycloalkanes Base, C1-C10Alkoxy, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30Heteroaryl；
R is expressed as structure shown in general formula (2), general formula (3) or general formula (4), the R and ring by way of be connected to general formula (1) in, asterisk indicates and the site of ring connection,
M and n is expressed as 0 or 1, and m+n >=1；
In general formula (3) and general formula (4), X1、X2And X3It is expressed as-O- ,-S- ,-C (R5)(R6) or-N (R7)-in one Kind；
R1、R2、R3、R5、R6、R7It is expressed as C1-C10Alkyl, C3-C10Naphthenic base, substituted or unsubstituted C6-C30Virtue Base, substituted or unsubstituted C2-C30Heteroaryl；
It is described " substituted " to refer at least one hydrogen atom by following substituent group to substitute: cyano, halogen atom, C1-C10 Alkyl, C3-C10Naphthenic base, C6-C30Aryl, C2-C30Heteroaryl；
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 general formula (1) is expressed as structure shown in general formula (1-1) or general formula (1-2):
As a further improvement of the present invention, the Ar1、Ar2、Ar3、Ar4、Ar5Independently be expressed as replace or Unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted dibiphenylyl, substituted or unsubstituted three Xenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted carbazyl, substituted or unsubstituted furyl, Substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, replace or Unsubstituted dibenzofuran group, substituted or unsubstituted fluorenyl, substituted or unsubstituted N- phenyl carbazole base, replace Or unsubstituted quinolines base, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolyl, replace or not One of substituted dibenzothiophene, substituted or unsubstituted naphthyridines base；The R1、R2、R3、R5、R6、R7Independently Ground be 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 substituent group is optionally from cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthalene One of base, xenyl, pyridyl group, dibenzofuran group, carbazyl or furyl are a variety of.
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 system of the organic compound with high mobility Preparation 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, be heated to reflux 12 hours, sample contact plate, fully reacting；From So cooling, filtering, filtrate revolving crosses silicagel column, obtains 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, has the feature that, includes anode Layer, cathode layer and organic function layer, the organic function layer is between the anode layer and cathode layer, the organic function layer Contain the organic compound.
As a further improvement of the present invention, the organic function layer includes electronic barrier layer or hole transmission layer, described Electronic barrier layer or hole transmission layer contain the organic compound
The fourth 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 middle energy saving ten thousand profit limited liability company in following preparation embodiments.
The synthesis of intermediate C1:
Specifically the preparation method is as follows: the raw material of 0.01mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml A1, addition 0.014mol raw material B1,0.03mol potassium tert-butoxide, 1.4 × 10-4molPd2(dba)3, 1.3 × 10-4Mol triphenyl Phosphine, 150ml toluene are heated to 100 DEG C and flow back 12 hours, samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving, Silicagel column is crossed, intermediate C1 is obtained；HPLC purity 98.7%, yield 86.8%；Elemental analysis structure (molecular formula C36H29N3): reason By 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 It is 503.24, measured value 503.22.
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 × 10-4molPd2(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 C55H43N3): reason By value C, 88.56；H,5.81；N,5.63；Test value: C, 88.57；H,5.82；N,5.63.ESI-MS (m/z) (M+): theoretical value It is 745.35, measured value 745.32.
The reaction class that the preparation step of reaction type and compound 1 that the preparation of remaining target compound is related to is related to Type is identical.
Prepare embodiment 2: the synthesis of compound 6
Prepare embodiment 3: the synthesis of compound 14
Prepare embodiment 4: the synthesis of compound 26
Prepare embodiment 5: the synthesis of compound 102
Prepare embodiment 6: the synthesis of compound 111
Prepare embodiment 7: the synthesis of compound 146
Prepare embodiment 8: the synthesis of compound 197
Prepare embodiment 9: the synthesis of compound 228
Prepare embodiment 10: the synthesis of compound 253
Prepare embodiment 11: the synthesis of compound 254
Prepare embodiment 12: the synthesis of compound 256
Prepare embodiment 13: the synthesis of compound 257
Prepare embodiment 14: the synthesis of compound 258
Prepare embodiment 15: the synthesis of compound 259
Prepare embodiment 16: the synthesis of compound 260
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 carry out hot property, T1 energy level, HOMO energy level, hole to the compounds of this invention respectively Mobility and Eg test, 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 software, 6-31G (d) base group, B3lyp functional, TD-FDT algorithm optimization geometry carry out HOMO, LUMO energy Grade calculates, 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.
Below by way of device embodiments 1~51 and device comparative example 1 compound that the present invention will be described in detail synthesizes in device The middle application effect as hole transmission layer or electronic barrier layer.Device embodiments 2~51, device comparative example 1 and device are implemented Example 1 is compared, and the manufacture craft of the device is identical, and uses identical baseplate material and electrode material, electrode The film thickness of material is also consistent, except that changing in device embodiments 2~25 to the material of hole transmission layer； The electronic blocking layer material of device is converted in device embodiments 26~51, the structure of each embodiment obtained device such as table 4 It is shown.
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 1,15,28 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 1,15,28 is the device architecture of material of the present invention and known materials collocation, and Device 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.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.

Claims (6)

1. a kind of organic compound with high mobility, which is characterized in that the structure of the organic compound such as general formula (1) institute Show:
In general formula (1), Ar1-Ar5It is expressed as substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30 Heteroaryl；
X is expressed as-O- ,-S- ,-C (R1)(R2) or-N (R3One of)-；
Z is expressed as C, N or C-R4；
R4It is expressed as hydrogen atom, protium atom, D-atom, tritium atom, halogen, cyano, C1-C10Alkyl, C3-C10Naphthenic base, C1- C10Alkoxy, substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C2-C30Heteroaryl；
R is expressed as structure shown in general formula (2), general formula (3) or general formula (4), the R and ring by way of be connected to general formula (1) In, asterisk indicates and the site of ring connection,
M and n is expressed as 0 or 1, and m+n >=1；
In general formula (3) and general formula (4), X1、X2And X3It is expressed as-O- ,-S- ,-C (R5)(R6) or-N (R7One of)-；
R1、R2、R3、R5、R6、R7It is expressed as C1-C10Alkyl, C3-C10Naphthenic base, substituted or unsubstituted C6-C30Aryl, Substituted or unsubstituted C2-C30Heteroaryl；
It is described " substituted " to refer at least one hydrogen atom by following substituent group to substitute: cyano, halogen atom, C1-C10Alkane Base, C3-C10Naphthenic base, C6-C30Aryl, C2-C30Heteroaryl；
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 general formula (1) is expressed as general formula (1-1) or logical Structure shown in formula (1-2):
3. organic compound according to claim 1, which is characterized in that the Ar1、Ar2、Ar3、Ar4、Ar5Independently Be expressed as substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted dibiphenylyl, take Generation or unsubstituted terphenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted carbazyl, replace or It is unsubstituted furyl, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substituted or unsubstituted Pyridazinyl, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted fluorenyl, substituted or unsubstituted N- benzene Base carbazyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoline azoles One of quinoline base, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthyridines base；
The R1、R2、R3、R5、R6、R7Separately it is expressed as methyl, isopropyl, tert-butyl, adamantyl, phenyl, biphenyl Base, naphthalene, dimethyl fluorenyl, dibenzofuran group, carbazyl, dibenzothiophene, pyridyl group, naphthyridines base or carbazole quinoline base.
The substituent group optionally from cyano, fluorine atom, methyl, ethyl, propyl, isopropyl, tert-butyl, amyl, phenyl, naphthalene, One of xenyl, pyridyl group, dibenzofuran group, carbazyl or furyl are a variety of.
4. 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.
5. a kind of organic electroluminescence device, includes anode layer, cathode layer and organic function layer, the organic function layer is located at institute It states between anode layer and cathode layer, which is characterized in that it is described in any item organic that the organic function layer contains claim 1-4 Compound.
6. a kind of organic electroluminescence device according to claim 4, 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 1-4 is described in any item to be had Machine compound.
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