CN109575012A - A kind of organic compound and its application containing fluorenes and pyridine diindyl - Google Patents
A kind of organic compound and its application containing fluorenes and pyridine diindyl Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
The present invention relates to a kind of organic compound containing fluorenes and pyridine diindyl and its application on organic electroluminescence device, the compound connects pyridyl group or pyrido indyl using five-membered ring fused benzene as core.The compounds of this invention glass transition temperature with higher and high bond dissociation energy, therefore can be improved the service life of OLED device；The compounds of this invention also has deep HOMO energy level and high electron mobility, it can be used as hole blocking layer/electron transport layer materials of OLED device or the material of inclined electron type main body, hole or energy can be effectively stopped to be transferred to electronic shell side from luminescent layer, to promote hole and electronics in the combined efficiency of luminescent layer, and then promote the luminous efficiency of OLED device.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of compound-material containing fluorenes and pyridine diindyl and
Its application in the field OLED.
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 there is good carrier mobility, high-vitrification conversion temperature etc., the main body material as luminescent layer
Material 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 present invention provides a kind of containing fluorenes and pyridine diindyl for the deficiency of the organic material in existing OLED device
Compound and its application.The compounds of this invention glass transition temperature with higher and high bond dissociation energy, deep HOMO energy level
With high electron mobility, can effectively stop hole or energy to be transferred to electronic shell side from luminescent layer, thus promoted hole and
Combined efficiency of the electronics in luminescent layer.
The technical scheme to solve the above technical problems is that
A kind of organic compound containing fluorenes and pyridine diindyl, shown in the structure such as general formula (1) of the organic compound:
General formula (1)
In general formula (1), R1And R2Separately indicate structure shown in pyridyl group or general formula (2), and R1And R2At least
There is one to be indicated by general formula (2)；
General formula (2)
In general formula (2), X1、X2、X3And X4Separately indicate N atom or CH, and X1、X2、X3And X4In be up to 2
Indicate N atom；
X5、X6、X7、X8And X9Separately indicate N atom or CH, and X5、X6、X7、X8And X9In be up to 2 expression N
Atom.
Preferably, general formula (1) is expressed as any one in structure:
The applicant additionally provides a kind of method for preparing the organic compound containing fluorenes and pyridine diindyl, preparation
The reaction equation occurred in the process is as follows:
Specific preparation process are as follows:
By compound R1- Br is added in anhydrous tetrahydro furan, is added dropwise n-butyllithium solution at -60~-85 DEG C, and reaction 20~
It 50 minutes, takes in Fluorenone THF dissolution injection constant pressure funnel, is added drop-wise in reactor, -60~-85 DEG C of reactions 1~5 are small
When, then normal-temperature reaction 12~24 hours；With water process, liquid separation is dry, and concentration, column chromatographs to obtain intermediate compound I；Wherein positive fourth
Base lithium and compound R1The molar ratio of-Br is (1.0~1.2): 1；Fluorenone and compound R1The molar ratio of-Br is (1.0~1.2):
1；
Intermediate compound I is dissolved in toluene, hydrobromic acid is added and is warming up to 90~110 DEG C, reaction 6~12 hours；Restore extremely
Room temperature adjusts pH to neutrality with sodium bicarbonate；Liquid separation, dry, column chromatographs to obtain intermediate II；Wherein HBr and compound R1- Br's
Molar ratio is (1.2~1.5): 1；
Intermediate II and intermediate III are dissolved in the mixed liquor of toluene and water, Pd (PPh is added after abundant deoxygenation3)4With
Potassium carbonate is warming up to 90~130 DEG C and reacts 12~24 hours；It is cooled to room temperature after reaction, liquid separation, dry, column chromatographs
To target compound；Wherein, the volume ratio of toluene and water is 5:1；The molar ratio of intermediate III and intermediate II be (1.1~
1.3):1；Pd(PPh3)4Molar ratio with intermediate II is (0.03~0.08): 1；The molar ratio of potassium carbonate and intermediate II is
(1.1~1.3): 1.
The applicant additionally provides a kind of organic electroluminescence device, includes hole blocking layer/electron transfer layer, described
It include the organic compound containing fluorenes and pyridine diindyl in hole blocking layer/electron transfer layer.Its structure includes under
The supreme transparent substrate layer being sequentially overlapped, anode layer, hole injection layer, hole transmission layer, luminescent layer, hole blocking layer/electronics
Transport layer, electron injecting layer, cathode layer.
The applicant additionally provides a kind of organic electroluminescence device, includes luminescent layer, includes power in the luminescent layer
Benefit require 1 or 2 described in the organic compound containing fluorenes and pyridine diindyl.
The beneficial effect of compound-material provided by the invention is:
The compound of the present invention connects pyrido indolyl radical, destroys molecular symmetry, avoid molecule using fluorenes as parent nucleus
Between aggtegation, have the characteristics that it is intermolecular be not easy to crystallize, be not easy to assemble, there is good filming, there is high vitrifying
Temperature and thermal stability, so, when the compounds of this invention is applied to OLED device, the film layer after can keeping material filming is stablized
Property, OLED device service life is improved, there is good application effect in OLED luminescent device, before there is good industrialization
Scape.
Since N atom has good electronic transmission performance, the compounds of this invention contains at least four N atom, therefore has good
Good electronic transmission performance, greatly improves luminescent properties.N atom can also influence HOMO energy level and the lumo energy of material with
And triplet distribution, the HOMO energy level material slightly lower compared with deep, T1 energy level can be used as hole blocking layer/electron transfer layer material
Material, HOMO energy level is shallower, the higher material of T1 energy level can be used as inclined electron type luminescent layer material of main part use.Simultaneously because N
The push-and-pull Electronic Performance of atom improves the bond dissociation energy (BDE) of compound, therefore the thermal stability and chemical stabilization of material
Property is all improved, and device lifetime increases considerably.
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, luminescent layer, 6, hole barrier/electron transfer layer, 7, electronics note
Enter layer 8, cathode reflection electrode layer.
Fig. 2 is the efficiency curve diagram that device measures at different temperatures.
Specific embodiment
The principle of the present invention and characteristic are described with reference to embodiments, for embodiment be served only for explaining this hair
It is bright, it is not intended to limit the scope of the present invention.
Embodiment 1: the synthesis of compound 1
The raw material 2- bromopyridine of 0.1mol is added in anhydrous tetrahydro furan, 110mL n-butyllithium solution is added dropwise at -78 DEG C
(1.0mol/L) reacts about 30 minutes, takes in the anhydrous THF dissolution injection constant pressure funnel of 0.1mol Fluorenone 50mL, is added dropwise
Into reactor, low-temp reaction 1 hour, then restore to room temperature reaction 12 hours；It is quenched and is reacted with water, liquid separation is dry, dense
Contracting, column chromatograph to obtain intermediate compound I -1；
The intermediate compound I -1 of 0.05mol is dissolved in 250mL toluene, in the hydrobromic acid (40%) that 50mL is added, is heated to
100 DEG C are reacted 12 hours.After reaction, restoring to room temperature, solution is adjusted to neutrality with sodium bicarbonate, liquid separation is dry, concentration,
Column is crossed to chromatograph to obtain intermediate II -1；
The intermediate II -1 of 0.03mol and intermediate III -1 are dissolved in the mixed solvent of toluene/water (100mL/20mL)
In, with the Pd (PPh that 0.0015mol is added after the abundant deoxygenation of nitrogen3)4With 0.05mol potassium carbonate, 100 DEG C are reacted 24 hours.Instead
Restore after answering to room temperature, liquid separation, dry, column chromatographs to obtain compound 1, purity: 99.5%, yield: 78%；
Elemental analysis structure (molecular formula C34H22N4): theoretical value C, 83.93；H,4.56；N,11.51；Test value: C,
83.97；H,4.51；N,11.48.ESI-MS(m/z)(M+): theoretical value 486.58, measured value 486.23.
Embodiment 2: the synthesis of compound 5
The preparation method is the same as that of Example 1 for compound 5, the difference is that replacing raw material 1 using raw material 2.
Elemental analysis structure (molecular formula C34H22N4): theoretical value C, 83.93；H,4.56；N,11.51；Test value: C,
83.95；H,4.53；N,11.47.ESI-MS(m/z)(M+): theoretical value 486.58, measured value 586.41.
Embodiment 3: the synthesis of compound 26
The preparation method is the same as that of Example 1 for compound 26, the difference is that replacing raw material 1 using raw material 3.
Elemental analysis structure (molecular formula C45H28N6): theoretical value C, 82.80；H,4.32；N,12.87；Test value: C,
82.84；H,4.35；N,12.81.ESI-MS(m/z)(M+): theoretical value 652.76, measured value 652.34.
Embodiment 4: the synthesis of compound 40
The preparation method is the same as that of Example 1 for compound 40, the difference is that replacing raw material 1 using raw material 4.
Elemental analysis structure (molecular formula C45H28N6): theoretical value C, 82.80；H,4.32；N,12.87；Test value: C,
82.85；H,4.33；N,12.84.ESI-MS(m/z)(M+): theoretical value 652.76, measured value 652.56.
The compounds of this invention is in organic electroluminescence device, as electron transfer layer or emitting layer material.To this hair
Bright compounds property test, test result are as shown in table 1:
Table 1
| Compound | Tg(℃) | Td(℃) | HOMO energy level (eV) | T1 energy level (eV) |
| Compound 1 | 143 | 432 | -5.94 | 2.75 |
| Compound 5 | 150 | 425 | -5.95 | 2.83 |
| Compound 26 | 141 | 412 | -5.83 | 2.73 |
| Compound 40 | 138 | 417 | -5.88 | 2.90 |
Note: triplet T1 is tested by the F4600 Fluorescence Spectrometer of Hitachi, and the test condition of material is 2*10-5's
Toluene solution；Glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimeter)
Measurement, 10 DEG C/min of heating rate；Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in Japanese Shimadzu Corporation
TGA-50H thermogravimetric analyzer on be measured, nitrogen flow 20mL/min；Highest occupied molecular orbital HOMO energy level be by
Ionizing energy test macro (IPS3) test, is tested as atmospheric environment.
By upper table data it is found that organic compound of the invention has different HOMO energy levels, different function can be applied to
Ergosphere, organic compound of the invention triplet with higher and higher thermal stability, so that made contains
The OLED device efficiency of organic compound of the present invention and service life get a promotion.
It is calculated by simulation, the calculating of bond dissociation energy (BDE), calculated result such as 2 institute of table has been carried out to compound 1 and 26
Show:
Table 2
Note: the software for calculation that bond dissociation energy BDE is used is Gauss 09, and the functional unit used is B3LYP/6-31G (d).
As can be seen from Table 2, the BDE value of the compounds of this invention molecular link, wherein neutral molecule is all 3.2 or more, sun from
Sub-key can be all 3.0 or more, and anion bond can be 2.8 or more, these all illustrate that the compounds of this invention possesses very high chemistry
Stability.
The resulting compound of above-described embodiment 1~4 is used to pass as the hole blocking layer of organic electroluminescence device/electronics
Defeated layer or luminescent layer have made device embodiments 1~4, and the manufacture craft of organic electroluminescence device is as follows:
Device embodiments 1
A) the ito anode layer 2 on transparent substrate layer 1 is cleaned, cleans each 15 with deionized water, acetone, EtOH Sonicate respectively
Minute, then handled 2 minutes in plasma cleaner；B) on ito anode layer 2, sky is deposited by vacuum evaporation mode
Layer material HAT-CN is injected in cave, and with a thickness of 10nm, this layer is as hole injection layer 3；C) on hole injection layer 3, pass through vacuum
Hole mobile material NPB is deposited in vapor deposition mode, and with a thickness of 60nm, which is hole transmission layer 4；D) on hole transmission layer 4
Luminescent layer 5 is deposited, uses CBP as material of main part, Ir (ppy)3As dopant material, Ir (ppy)3Mass ratio with CBP is
10:90, with a thickness of 30nm；E) on luminescent layer 5, the compounds of this invention 1 is deposited by vacuum evaporation mode, with a thickness of
40nm, this layer of organic material are used as hole barrier/electron transfer layer 6；F) on hole barrier/electron transfer layer 6, very
Sky vapor deposition electron injecting layer LiF, with a thickness of 1nm, which is electron injecting layer 7；G) on electron injecting layer 7, vacuum evaporation
Cathode Al (100nm), the layer are cathode reflection electrode layer 8.
The molecular structural formula of associated materials is as follows:
Device embodiments 2
The manufacture craft of the device compared with device embodiments 1 of device embodiments 2 is identical, and used phase
Same baseplate material and electrode material, the film thickness of electrode material is also consistent, the difference is that the electroluminescent hair of device embodiments 2
Hole barrier/electron transport layer materials of optical device are TPBI, and the luminescent layer material of main part of electroluminescent device becomes the present invention
Compound 5, dopant material are Ir (ppy)3, compound 5 and Ir (ppy)3Mass ratio be 90:10.
Device embodiments 3
The manufacture craft of the device compared with device embodiments 1 of device embodiments 3 is identical, and used phase
Same baseplate material and electrode material, the film thickness of electrode material is also consistent, the difference is that the electroluminescent hair of device embodiments 3
Hole barrier/electron transport layer materials of optical device are the compounds of this invention 26.
Device embodiments 4
The manufacture craft of the device compared with device embodiments 1 of device embodiments 4 is identical, and used phase
Same baseplate material and electrode material, the film thickness of electrode material is also consistent, the difference is that the electroluminescent hair of device embodiments 4
Hole barrier/electron transport layer materials of optical device are TPBI, and the luminescent layer material of main part of electroluminescent device becomes the present invention
Compound 40 and compound GH, dopant material are Ir (ppy)3, compound 40, GH and Ir (ppy)3Three's mass ratio is 50:
40:10。
Device comparative example 1: hole barrier/electron transport layer materials of electroluminescent device are TPBI, electroluminescent device
Luminescent layer material of main part be known compound CBP, dopant material be Ir (ppy)3, Ir (ppy)3Mass ratio with CBP is 10:
90。
After the production of above-mentioned electroluminescent device, the current efficiency of measurement device and service life, the result is shown in shown in table 3.
Table 3
| Device | Open bright voltage (V) | Luminous efficiency (cd/A) | Service life (LT95, h) | CIE(x,y) |
| Device embodiments 1 | 3.8 | 48.2 | 40.3 | (0.32,0.64) |
| Device embodiments 2 | 3.7 | 46.4 | 45.8 | (0.31,0.64) |
| Device embodiments 3 | 4.0 | 50.5 | 46.9 | (0.32,0.65) |
| Device embodiments 4 | 3.8 | 54.9 | 48.1 | (0.31,0.62) |
| Device comparative example 1 | 4.9 | 28 | 10.5 | (0.33,0.63) |
Note: life-span test system is owner of the present invention and the OLED device life test that Shanghai University is studied jointly
Instrument.
By the result of table 3 can be seen that the compounds of this invention can be applied to OLED luminescent device production, and with device ratio
It is compared compared with example 1, either opens the change more larger than the acquisition of known OLED material of bright voltage, efficiency or service life.
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 1,3 and device comparative example 1 and carries out efficiency test in -10~80 DEG C of sections, acquired results are as shown in table 4 and Fig. 2.
Table 4
From the data of table 4 and Fig. 2 it is found that device embodiments 1,3 are material of the present invention and the device junction that known materials are arranged in pairs or groups
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.
The foregoing is merely presently preferred embodiments of the present 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 (6)
1. a kind of organic compound containing fluorenes and pyridine diindyl, which is characterized in that the structure such as general formula of the organic compound
(1) shown in:
In general formula (1), R1And R2Separately indicate structure shown in pyridyl group or general formula (2), and R1And R2At least one
It is a to be indicated by general formula (2)；
In general formula (2), X1、X2、X3And X4Separately indicate N atom or CH, and X1、X2、X3And X4In be up to 2 expression N
Atom；
X5、X6、X7、X8And X9Separately indicate N atom or CH, and X5、X6、X7、X8And X9In be up to 2 expression N atoms.
2. organic compound according to claim 1, which is characterized in that general formula (1) is expressed as any in structure
It is a kind of:
3. a kind of method for preparing the organic compound of any of claims 1 or 2 containing fluorenes and pyridine diindyl, it is characterised in that
The reaction equation occurred in preparation process is as follows:
Specific preparation process are as follows:
By compound R1- Br is added in anhydrous tetrahydro furan, and n-butyllithium solution is added dropwise at -60~-85 DEG C, reacts 20~50 points
Clock, take Fluorenone THF dissolution injection constant pressure funnel in, be added drop-wise in reactor, -60~-85 DEG C react 1~5 hour, so
Normal-temperature reaction 12~24 hours afterwards；With water process, liquid separation is dry, and concentration, column chromatographs to obtain intermediate compound I；Wherein n-BuLi with
Compound R1The molar ratio of-Br is (1.0~1.2): 1；Fluorenone and compound R1The molar ratio of-Br is (1.0~1.2): 1；
Intermediate compound I is dissolved in toluene, hydrobromic acid is added and is warming up to 90~110 DEG C, reaction 6~12 hours；Restore to room temperature,
PH is adjusted to neutrality with sodium bicarbonate；Liquid separation, dry, column chromatographs to obtain intermediate II；Wherein HBr and compound R1Mole of-Br
Than for (1.2~1.5): 1；
Intermediate II and intermediate III are dissolved in the mixed liquor of toluene and water, Pd (PPh is added after abundant deoxygenation3)4And carbonic acid
Potassium is warming up to 90~130 DEG C and reacts 12~24 hours；It is cooled to room temperature after reaction, liquid separation, dry, column chromatographs to obtain mesh
Mark compound；Wherein, the volume ratio of toluene and water is 5:1；The molar ratio of intermediate III and intermediate II is (1.1~1.3):
1；Pd(PPh3)4Molar ratio with intermediate II is (0.03~0.08): 1；The molar ratio of potassium carbonate and intermediate II be (1.1~
1.3):1。
4. a kind of organic electroluminescence device, which is characterized in that it include hole blocking layer/electron transfer layer, the hole resistance
It include the organic compound of any of claims 1 or 2 containing fluorenes and pyridine diindyl in barrier/electron transfer layer.
5. a kind of organic electroluminescence device, which is characterized in that include luminescent layer, include claim 1 in the luminescent layer
Or the organic compound described in 2 containing fluorenes and pyridine diindyl.
6. organic electroluminescence device according to claim 4, which is characterized in that its structure includes successively folding from bottom to up
Transparent substrate layer, anode layer, hole injection layer, hole transmission layer, luminescent layer, the hole blocking layer/electron transfer layer, electronics added
Implanted layer, cathode layer.
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