CN109942439A - A kind of tri-arylamine group organic compound and its application - Google Patents
A kind of tri-arylamine group organic compound and its application Download PDFInfo
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Abstract
The present invention relates to a kind of tri-arylamine group organic compound and its applications, belong to technical field of semiconductors, and the present invention provides the structure of organic compound as shown in logical formula (I):Organic compound provided by the invention has stronger cavity transmission ability, under appropriate HOMO energy level, improves hole injection and transmission performance；Under suitable lumo energy, and play the role of electronic blocking, promotes combined efficiency of the exciton in luminescent layer；When light emitting functional layer materials'use as OLED luminescent device, the branch in the scope of the invention of arranging in pairs or groups can effectively improve exciton utilization rate and radiation efficiency.
Description
Technical field
The present invention relates to technical field of semiconductors more particularly to a kind of tri-arylamine group organic compound and its applications.
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.Structure of the OLED luminescent device like sandwich, including electrode material film layer, and it is clipped in different electricity
Organic functional material between the film layer of pole, various different function materials are overlapped mutually depending on the application collectively constitutes OLED hair together
Optical device.As current device, when the two end electrodes application voltage to OLED luminescent device, and pass through electric field action organic layer function
Positive and negative charge in energy film layer, positive and negative charge is further compound in luminescent layer, i.e. generation OLED electroluminescent.
Currently, OLED display technology in smart phone, applied by the fields such as tablet computer, further will also be to electricity
Depending on etc. large scales application field extension, still with actual products application require compare, the luminous efficiency of OLED device, use
The performances such as service life also need further to be promoted.Proposing high performance research for OLED luminescent device includes: to reduce the driving of device
Voltage improves the luminous efficiency of device, improves the service life etc. of device.In order to realize that the continuous of performance of OLED device mentions
It rises, not only needs the innovation from OLED device structure and manufacture craft, constantly study and create with greater need for oled light sulfate ferroelectric functional material
Newly, the functional material of higher performance OLED is formulated out.
Oled light sulfate ferroelectric functional material applied to OLED device can be divided into two major classes, i.e. charge injection transmission from purposes
Material and luminescent material further can also 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 that various organic functional materials have good photoelectric characteristic,
For example, as charge transport materials, it is desirable that have good carrier mobility, high-vitrification conversion temperature etc., as luminous
The material of main part of layer requires material to have good bipolarity, HOMO/LUMO energy rank appropriate etc..
The oled light sulfate ferroelectric functional material film layer for constituting OLED device includes at least two layers or more structure, applies in industry
OLED device structure then includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics biography
A variety of film layers such as defeated layer, electron injecting layer, that is to say, that the photoelectric functional material applied to OLED device is infused including at least hole
Enter material, hole mobile material, luminescent material, electron transport material etc., material type and collocation form with rich and more
The characteristics of sample.In addition, used photoelectric functional material has stronger for the collocation of the OLED device of different structure
Selectivity, performance of the identical material in different structure device, it is also possible to completely totally different.
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, and OLED functional material or combination of materials with high performance are just able to achieve device
High 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
The applicant provides a kind of tri-arylamine group organic compound and its applications.Organic compound of the present invention has
Higher glass transition temperature and molecule thermal stability, suitable HOMO energy level, are optimized by device architecture, can effectively be promoted
The photoelectric properties of OLED device and the service life of OLED device.
Specific technical solution of the present invention is as follows: a kind of tri-arylamine group organic compound, the structure of the organic compound is such as
Shown in logical formula (I):
The Ar1、Ar2、Ar3、Ar4、Ar5It each independently represents as substituted or unsubstituted C6-C30Aryl, replace
Or unsubstituted C2-C30Heteroaryl；
The R1、R2Independently be expressed as 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-C10
Alkyl, C3-C10Naphthenic base, C6-C30Aryl, C2-C30Heteroaryl；
Hetero atom is optionally from one of oxygen atom, sulphur atom or nitrogen-atoms or a variety of in the heteroaryl.
As a further improvement of the present invention, it is any to general formula (I-4) to be represented by general formula (I-1) for the logical formula (I)
Shown structure:
As a further improvement of the present invention, Ar in the logical formula (I)1And Ar4For identical group, Ar2And Ar3For phase
Same group.
As a further improvement of the present invention, the Ar1、Ar2、Ar3、Ar4、Ar5、R1、R2Optionally from phenyl, xenyl,
Naphthalene, thienyl, dimethyl fluorenyl, diphenyl fluorenyl, Spirofluorene-based, dibenzofuran group, carbazyl, dibenzothiophene, pyrrole
Piperidinyl, naphthyridines base or carbazole quinoline base.
As a further improvement of the present invention, the substituent group is optionally from cyano, fluorine atom, methyl, isopropyl, tertiary fourth
Base, adamantyl, phenyl, xenyl, naphthalene, dimethyl fluorenyl, diphenyl fluorenyl, Spirofluorene-based, dibenzofuran group, carbazole
One of base, dibenzothiophene, pyridyl group, naphthyridines base or carbazole quinoline base are a variety of.
As a further improvement of the present invention, the organic compound specific structure are as follows:
A kind of organic electroluminescence device, includes anode, cathode and organic function layer, and the organic function layer is located at described
Between anode and cathode, the organic function layer contains the tri-arylamine group organic compound.
As a further improvement of the present invention, the organic function layer includes hole transmission layer or electronic barrier layer, described
Hole transmission layer or electronic barrier layer contain the tri-arylamine group organic compound.
A kind of illumination or display element, including the organic electroluminescence device.
Compared with prior art, the present invention is beneficial has the technical effect that
(1) the compound of the present invention hole mobility with higher, hole transmission layer as OLED luminescent device
Combined efficiency of the exciton in luminescent layer can be improved in material, capacity usage ratio is improved, to improve device light emitting efficiency.
(2) the compound of the present invention balances electrons and holes more in the distribution of luminescent layer, in appropriate HOMO energy
Under grade, hole injection and transmission performance are improved；Under suitable lumo energy, and play the role of electronic blocking, is promoted
Combined efficiency of the exciton in luminescent layer；Exciton utilization rate can be effectively improved, device voltage is reduced, improves the current efficiency of device
And the service life.The compound of the present invention has good application effect in OLED luminescent device, has good industrialization prospect.
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 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transport, and 5 be electronic blocking
Layer, 6 be luminescent layer, and 7 be electron-transport or hole blocking layer, and 8 be electron injecting layer, and 9 be cathode reflection electrode layer, and 10 take for light
Layer out.
Fig. 2 is the current efficiency variation with temperature curve of device of the present invention.
Specific embodiment
All raw materials are purchased in Fine Chemical Industry Co in following preparation embodiments.
Embodiment 1: the synthesis of intermediate A -1
The raw material II of 0.01mol raw material I, 0.012mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml,
0.03mol potassium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4Mol triphenylphosphine, 150ml toluene, 130 DEG C are heated to reflux
12 hours, sample contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate A -1；Elemental analysis
Structure (molecular formula C21H19N): theoretical value C, 88.38；H,6.71；N,4.91；Test value: C, 88.39；H,6.70；N,4.91.
ESI-MS(m/z)(M+): theoretical value 285.39, measured value 285.44.
Intermediate A is prepared with the synthetic method of intermediate A -1, specific structure is as shown in table 1.
Table 1
Embodiment 2: the synthesis of compound 4
The intermediate of 0.01mol raw material II I, 0.012mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml
A-1,0.03mol potassium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4Mol triphenylphosphine, 150ml toluene, 130 DEG C of heating
Reflux 12 hours samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate B -1；Element
Analyze structure (molecular formula C21H39BrN2): theoretical value C, 79.66；H,5.43；Br,11.04；N,3.87；Test value: C, 79.68；
H,5.44；Br,11.02；N,3.86.ESI-MS(m/z)(M+): theoretical value 723.76, measured value 723.85.
The centre of 0.01mol intermediate B -1,0.012mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml
Body A-2,0.03mol potassium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4Mol triphenylphosphine, 150ml toluene, 150 DEG C add
Heat reflux 18 hours, samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain compound 4；Member
Element analysis structure (molecular formula C72H57N3): theoretical value C, 89.68；H,5.96；N,4.36；Test value: C, 89.67；H,5.95；N,
4.38；.ESI-MS(m/z)(M+): theoretical value 964.27, measured value 964.57.
The preparation method of embodiment 3-15 is similar with the preparation method of embodiment 2, and relevant technical staff in the field can basis
Conventional technical means carries out adjustment appropriate, the raw material that preparation embodiment 3-15 is used to the amount of raw material and the ratio of reactant
III, intermediate A, the specific structure of intermediate B and product are as shown in table 2.
Table 2
Embodiment 16: the synthesis of compound 212
The intermediate of 0.01mol raw material II I, 0.012mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml
A-3,0.03mol potassium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4Mol triphenylphosphine, 150ml toluene, 120 DEG C of heating
Reflux 10 hours samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate B -15；Member
Element analysis structure (molecular formula C18H13Br2N): theoretical value C, 53.63；H,3.25；Br,39.64；N,3.47；Test value: C,
53.64；H,3.26；Br,39.65；N,3.46.ESI-MS(m/z)(M+): theoretical value 403.12, measured value 403.15.
The centre of 0.01mol intermediate B -15,0.012mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml
Body A-24,0.03mol potassium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4Mol triphenylphosphine, 150ml toluene, 130 DEG C add
Heat reflux 12 hours, samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain intermediate B -16；
Elemental analysis structure (molecular formula C45H35BrN2): theoretical value C, 79.06；H,5.16；Br,11.69；N,4.10；Test value: C,
79.04；H,5.15；Br,11.69；N,4.13.ESI-MS(m/z)(M+): theoretical value 683.69, measured value 683.75.
The centre of 0.01mol intermediate B -16,0.012mol is added under the atmosphere for being passed through nitrogen in the there-necked flask of 250ml
Body A-5,0.03mol potassium tert-butoxide, 1 × 10-4molPd2(dba)3, 1 × 10-4Mol triphenylphosphine, 150ml toluene, 150 DEG C add
Heat reflux 12 hours, samples contact plate, fully reacting；Natural cooling, filtering, filtrate revolving cross silicagel column, obtain compound 212；
Elemental analysis structure (molecular formula C69H53N3): theoretical value C, 89.67；H,5.78；N,4.55；Test value: C, 89.65；H,5.79；
N,4.56。ESI-MS(m/z)(M+): theoretical value 924.20, measured value 924.45.
Embodiment 17: the synthesis of compound 216
The synthesis step of compound 216 is similar to the synthesis step of compound 212, only by the intermediate of intermediate A -24
A-1 is replaced, and intermediate A -5 is replaced with intermediate A -2；
Elemental analysis structure (molecular formula C63H49N3): theoretical value C, 89.22；H,5.82；N,4.95；Test value: C,
89.20；H,5.81；N,4.98.ESI-MS (m/z) (M+): theoretical value 848.11, measured value 848.47.
The compounds of this invention uses in luminescent device, can be used as hole transport layer material, can also be used as electronics resistance
Barrier materials'use.Hot property, T1 energy level, HOMO energy level and sky are carried out respectively to the compound of the above embodiment of the present invention preparation
The test of cave mobility, testing result are as 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/mL；By differential scanning calorimetry, (DSC, German Nai Chi company DSC204F1 show glass transition temperature Tg
Difference scanning calorimeter) measurement, 10 DEG C/min of heating rate；Highest occupied molecular orbital HOMO energy level is to be tested to be by ionizing energy
System (IPS-3) test, is tested as atmospheric environment；Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the day island proper
It is measured on the TGA-50H thermogravimetric analyzer of saliva company, nitrogen flow 20mL/min；Hole mobility test, this is sent out
Single charge devices are made in bright material, are measured with SCLC method.
By upper table data it is found that organic compound of the invention has more appropriate HOMO energy level, hole can be applied to
Transport layer or electronic barrier layer, organic compound of the invention hole mobility with higher and higher thermal stability, make
Made the OLED device efficiency containing organic compound of the present invention and service life is obtained to get a promotion.
Below by way of device embodiments 1-25 and device comparative example 1 OLED material that the present invention will be described in detail synthesizes in device
In application effect.The production work of device embodiments 2-25 and device comparative example 1 device compared with device embodiments 1 of the present invention
Skill is identical, and uses identical baseplate material and electrode material, and the film thickness of electrode material is also consistent, and institute is not
Be in device hole transport layer material or electronic blocking layer material replace.The structure of each embodiment obtained device
Composition is as shown in table 4.Current efficiency, color and the 10mA/cm of each embodiment obtained device2The test in the LT97 service life under electric current
The results are shown in Table 5.The efficiency attenuation coefficient of obtained deviceTest result it is as shown in table 6.The testing current knot of obtained device
Fruit is as shown in table 7.
Device embodiments 1
As shown in Figure 1, transparent substrate layer 1 is transparent PI film, ito anode layer 2 (film thickness 150nm) is washed, i.e.,
Neutralizing treatment, pure water, drying are successively carried out, then carries out ultraviolet-ozone washing to remove the organic residue on the transparent surface ITO
Object.On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, the HAT-CN that film thickness is 10nm is deposited
It is used as hole injection layer 3.Then the compound 4 that 60nm thickness is deposited is used as hole transmission layer 4.Then vapor deposition 20nm thickness
Compound EB-1 as electronic barrier layer 5.After above-mentioned hole mobile material vapor deposition, production OLED luminescent device shines
Layer 6, structure include OLED luminescent layer 6 used GH-1, GH-2 as material of main part, and GD-1 adulterates material as dopant material
Material doping ratio is 10% weight ratio, and luminescent layer film thickness is 30nm.After above-mentioned luminescent layer 6, continues vacuum evaporation electronics and pass
Defeated layer material is ET-1 and Liq.The vacuum evaporation film thickness of the material is 30nm, this layer is hole barrier/electron transfer layer 7.?
On hole barrier/electron transfer layer 7, by vacuum deposition apparatus, lithium fluoride (LiF) layer that film thickness is 1nm is made, this layer is electricity
Sub- implanted layer 8.On electron injecting layer 8, by vacuum deposition apparatus, the Mg:Ag electrode layer that film thickness is 15nm is made, this layer is
Cathode layer 9.On cathode layer 9, the CP-1 of vacuum evaporation 70nm, as CPL layer 10.OLED luminescent device is completed as described above
Afterwards, anode and cathode is connected with well known driving circuit, the current efficiency of measurement device and the service life of device, as a result
As shown in table 5.
Table 4
Table 5
Note: LT97 refers to that in current density be 10mA/cm2In the case of, device brightness decay to 97% used in the time；
Life-span test system is Japan System Engineer's Co., the OLED of the model EAS-62C of LTD exploitation
Device lifetime tester.
It can be seen from the device data result of table 5 compared with device comparative example 1, organic luminescent device of the invention without
By being to obtain biggish promotion both with respect to the OLED device of known materials in efficiency or service life.
In order to compare different components at higher current densities efficiency decay the case where, define efficiency attenuation coefficientCarry out table
Show, it indicates that driving current is 100mA/cm2When device maximal efficiency μ 100 and the difference of maximal efficiency μm of device and maximum
Ratio between efficiency,Value is bigger, illustrates that the efficiency roll-off of device is more serious, conversely, illustrating that device is fast at higher current densities
Speed the problem of dropping of declining is under control.Efficiency attenuation coefficient is carried out respectively to device embodiments 1-25 and device comparative example 1Survey
Fixed, testing result is as shown in table 6:
Table 6
From the point of view of the data of table 6, compared by the efficiency attenuation coefficient of embodiment and comparative example it will be seen that this hair
Bright organic luminescent device can be effectively reduced efficiency roll-off.
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 3,10,15 and device comparative example 1 and carries out efficiency test in -10~80 DEG C of sections, acquired results are as shown in Table 7 and Fig. 2.
Table 7
From the data of table 7 and Fig. 2 it is found that device embodiments 3,10,15 are material of the present invention and the device that known materials are arranged in pairs or groups
Part structure is compared with device comparative example 1, and not only Efficiency at Low Temperature is high, but also in temperature elevation process, efficiency is steadily increased.
To sum up, the foregoing is merely a prefered embodiment of the invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (9)
1. a kind of tri-arylamine group organic compound, which is characterized in that the structure of the organic compound is as shown in logical formula (I):
The Ar1、Ar2、Ar3、Ar4、Ar5It each independently represents as substituted or unsubstituted C6-C30Aryl, replace or not
Substituted C2-C30Heteroaryl；
The R1、R2Independently be 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: cyano, halogen atom, C1-C10Alkane
Base, C3-C10Naphthenic base, C6-C30Aryl, C2-C30Heteroaryl；
Hetero atom is optionally from one of oxygen atom, sulphur atom or nitrogen-atoms or a variety of in the heteroaryl.
2. organic compound according to claim 1, which is characterized in that the logical formula (I) is represented by general formula (I-1) extremely
Structure shown in general formula (I-4) is any:
3. organic compound according to claim 1, which is characterized in that Ar in the logical formula (I)1And Ar4For identical base
Group, Ar2And Ar3For identical group.
4. organic compound according to claim 1, which is characterized in that the Ar1、Ar2、Ar3、Ar4、Ar5、R1、R2Optionally
From phenyl, xenyl, naphthalene, thienyl, dimethyl fluorenyl, diphenyl fluorenyl, Spirofluorene-based, dibenzofuran group, carbazyl, two
Benzothienyl, pyridyl group, naphthyridines base or carbazole quinoline base；
5. organic compound according to claim 1, which is characterized in that the substituent group is optionally from cyano, fluorine atom, first
Base, isopropyl, tert-butyl, adamantyl, phenyl, xenyl, naphthalene, dimethyl fluorenyl, diphenyl fluorenyl, Spirofluorene-based, hexichol
And one of furyl, carbazyl, dibenzothiophene, pyridyl group, naphthyridines base or carbazole quinoline base or a variety of.
6. organic compound according to claim 1, which is characterized in that the organic compound specific structure are as follows:
7. a kind of organic electroluminescence device, includes anode, cathode and organic function layer, the organic function layer is located at the sun
Between pole and cathode, which is characterized in that the organic function layer is containing the described in any item tri-arylamine group organic compounds of 1-6 of having the right
Object.
8. organic electroluminescence device according to claim 5, the organic function layer includes hole transmission layer or electronics
Barrier layer, which is characterized in that the hole transmission layer or electronic barrier layer contain triaryl amine described in any one of claims 1-6
Class organic compound.
9. a kind of illumination or display element, which is characterized in that including the described in any item organic electroluminescents of claim 7 or 8
Device.
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Application publication date: 20190628 |