CN106467511A - A kind of compound with acridone as core and its application on organic electroluminescence device - Google Patents
A kind of compound with acridone as core and its application on organic electroluminescence device Download PDFInfo
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Abstract
The invention discloses a kind of compound with acridone as core and its application on organic electroluminescence device, this compound, with acridone as core, has the characteristics that intermolecular be difficult crystallization, be difficult to assemble, have good filming.When the compounds of this invention uses as the emitting layer material of OLED luminescent device, the current efficiency of device, power efficiency and external quantum efficiency are all greatly improved；Lifted clearly simultaneously for device lifetime.
Description
Technical field
The present invention relates to technical field of semiconductors, especially relate to a kind of compound with acridone as core, Yi Jiqi
As application on Organic Light Emitting Diode for the emitting layer material.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to make
Make new display product it is also possible to be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is quite varied.
OLED luminescent device just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute OLED luminescent device together.
As current device, when the two end electrodes applied voltage to OLED luminescent device, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is compound in luminescent layer further, that is, produce OLED electroluminescent.
Organic Light Emitting Diode (OLEDs) large-area flat-plate show and illumination in terms of application cause industrial quarters and
The extensive concern of art circle.However, traditional organic fluorescence materials can only be lighted using 25% singlet exciton being electrically excited formation, device
The internal quantum efficiency of part is relatively low (being up to 25%).External quantum efficiency is generally less than 5%, also very big with the efficiency of phosphorescent devices
Gap.Although phosphor material enhances intersystem crossing due to the strong SO coupling in heavy atom center, can with effectively utilizes electricity
Excite singlet exciton and the Triplet exciton of formation, make the internal quantum efficiency of device reach 100%.But phosphor material exists
Expensive, stability of material is poor, limits its application in OLEDs the problems such as device efficiency tumbles serious.Hot activation is prolonged
Fluorescence (TADF) material is the third generation luminous organic material of development after organic fluorescence materials and organic phosphorescent material late.Should
Class material typically has poor (the △ E of little singletstate-tripletST), triplet excitons can be changed by anti-intersystem crossing
Singlet exciton is become to light.This can make full use of the singlet exciton being electrically excited lower formation and triplet excitons, device interior
Quantum efficiency can reach 100%.Meanwhile, material structure is controlled, stable in properties, low price without precious metal, in OLEDs
The having a extensive future of field.
Although TADF material can realize 100% exciton utilization rate in theory, there are in fact following problem：(1)
T1 the and S1 state of design molecule has strong CT feature, and very little S1-T1 state energy gap is although can be realized by TADF process
High T1→S1State exciton conversion ratio, but also result in low S1 state radiation transistion speed, consequently it is difficult to have (or realizing) concurrently simultaneously
High exciton utilization rate and high fluorescent radiation efficiency；(2) even if having adopted doping device to mitigate T exciton concentration quenching effect, greatly
Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For the actual demand that current OLED shows Lighting Industry, the development of current OLED material is also far from enough, falls
After the requirement of panel manufacturing enterprise, the organic functional material as material enterprise development higher performance is particularly important.
Content of the invention
For prior art exist the problems referred to above, the applicant provide a kind of compound with acridone as core and
Its application on organic electroluminescence device.The compounds of this invention is based on TADF mechanism with acridone as core, as luminous
Layer material is applied to Organic Light Emitting Diode, and the device that the present invention makes has good photoelectric properties, disclosure satisfy that panel system
Make the requirement of enterprise.
Technical scheme is as follows：
The applicant provides a kind of compound with acridone as core it is characterised in that described compound structure is as led to
Shown in formula (1)：
In formula (1), Ar is expressed as Ar1R or R；Wherein, Ar1Represent phenyl, dibiphenylyl, terphenyl or naphthyl；
R chooses formula (2) or structure shown in formula (3)：
Wherein, Ar2Represent phenyl, C1-10Straight or branched alkyl replace phenyl, dibiphenylyl, terphenyl, naphthyl,
Or anthryl；R1、R2、R3Selection carbon atom independently is the alkyl of 1-10, carbon atom is 4-20 without heteroatomic fragrance
Base, formula (4), formula (5), formula (6) or structure shown in formula (7)；R2、R3It is asynchronously hydrogen；
Ar3、Ar4、Ar5Expression C independently1-10The substituted or unsubstituted phenyl of straight or branched alkyl, xenyl,
Terphenyl, naphthyl or anthryl；X1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The alkylene that straight or branched alkyl replaces
One of tertiary amine groups that base, the alkylidene of aryl replacement, alkyl or aryl replace.
Preferably, R3It is expressed as formula (4), formula (6) or shown in formula (7) during structure, R2It is expressed as hydrogen atom.
Preferably, in formula (1), R specifically can be chosen for：
In any one.
Preferably, the concrete structure formula of described compound is：
In any one.
The applicant additionally provides a kind of luminescent device comprising described compound, and described compound is as the master of luminescent layer
Body material, for making OLED.
The applicant additionally provides a kind of luminescent device comprising described compound, described compound mixing as luminescent layer
Miscellaneous material, for making OLED.
The applicant additionally provides a kind of method preparing described compound, and the reaction equation in preparation process is：
Specifically preparation process is：
Take Ar-Br and acridone, dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, sodium tert-butoxide；In inertia
Under atmosphere, the mixed solution of above-mentioned reactant is reacted 10～24 hours at 95～110 DEG C of temperature, then cool down and filter anti-
Answer solution, filtrate revolving, cross silicagel column, obtain target product；
Described Ar-Br is 1 with the mol ratio of acridone:2.0～3.0, Pd2(dba)3Mol ratio with Ar-Br is 0.006
～0.02:1, tri-butyl phosphine is 0.006～0.02 with the mol ratio of Ar-Br:1, sodium tert-butoxide with the mol ratio of Ar-Br is
1.0～3.0:1.
Beneficial the having technical effect that of the present invention：
The compounds of this invention, with acridone as parent nucleus, nitrogen-atoms reconnects an aromatic heterocycle group, destroys molecule
Symmetry, thus the crystallinity of saboteur, material is more stable during evaporation, be deposited with process homogeneous film formation, it is to avoid point
Aggregation between son, mostly is rigid radical in molecule, the heat stability of material very well, the film property having had and fluorescent quantum
Efficiency, can use as luminescent layer dopant material；Described compound structure intramolecular comprises electron donor (donor, D) and electricity
The combination of sub- receptor (acceptor, A) can increase Orbital Overlap, improve luminous efficiency, be simultaneously connected with aromatic heterocycle group with
Obtain the charge transfer state material that HOMO, LUMO are spatially separating, realize the energy level difference of little S1 state and T1 state, thus in thermostimulation
Under the conditions of realize reverse intersystem crossing, be suitable as luminescent layer material of main part use.
Compound of the present invention can as emitting layer material be applied to OLED luminescent device make, and respectively as send out
Photosphere material of main part and dopant material, all can obtain good device performance, the current efficiency of device, power efficiency and outer amount
Sub- efficiency is all greatly improved；Lifted clearly simultaneously for device lifetime.Compound-material of the present invention is in OLED
There is in luminescent device good application effect, there is good industrialization prospect.
Brief description
Fig. 1 is the device architecture schematic diagram using the compounds of this invention；
Wherein, 1 is transparent substrate layer, and 2 is ito anode layer, and 3 is hole injection layer, and 4 is hole transmission layer, and 5 is luminous
Layer, 6 is electron transfer layer, and 7 is electron injecting layer, and 8 is negative electrode reflection electrode layer.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of embodiment 1 compound 2
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, the addition bromo- 9- of 0.01mol 3- (3,5- 3,5-dimethylphenyl)-
6- (hexichol amido) carbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol
Tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filter, filtrate revolving,
Cross silicagel column, obtain target product, purity 99.60%, yield 57.32%.
Identify this compound, molecular formula C using DEI-MS45H33N3O, detected value [M+1]+=631.42, value of calculation
631.26.
The synthesis of embodiment 2 compound 4
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, the addition bromo- 9- of 0.01mol 3- (3,5- diphenyl phenyl)-
6- tert-butyl carbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri- uncle
Butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filters, filtrate revolving, cross silicon
Glue post, obtains target product, purity 99.62%, yield 62.32%.
Identify this compound, molecular formula C using DEI-MS47H36N2O, detected value [M+1]+=644.52, value of calculation
644.28.
The synthesis of embodiment 3 compound 7
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol 3- bromo- 9- phenyl -6- acridinyl click
Azoles, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine,
150ml toluene, is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling, filters, filtrate revolving, crosses silicagel column, obtains
To target product, purity 99.52%, yield 64.42%.
Identify this compound, molecular formula C using DEI-MS46H33N3O, detected value [M+1]+=643.58, value of calculation
643.26.
The synthesis of embodiment 4 compound 8
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol 3- bromo- 9- phenyl -6- phenazinyl click
Azoles, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine,
150ml toluene, is heated to reflux 24 hours, sample point plate, and reaction is complete, natural cooling, filters, filtrate revolving, crosses silicagel column, obtains
To target product, purity 99.55%, yield 61.41%.
Identify this compound, molecular formula C using DEI-MS43H27N3O2, detected value [M+1]+=617.43, value of calculation
617.21.
The synthesis of embodiment 5 compound 13
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol 3,6- bis- (hexichol amido) -9- (4- bromine
Phenyl) carbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The tertiary fourth of mol tri-
Base phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filters, filtrate revolving, cross silica gel
Post, obtains target product, purity 99.58%, yield 61.71%.
Identify this compound, molecular formula C using DEI-MS55H38N4O, detected value [M+1]+=770.52, value of calculation
770.30.
The synthesis of embodiment 6 compound 17
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol 3,6- bis- (carbazyl) -9- (4- bromobenzene
Base) carbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert
Phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filters, filtrate revolving, cross silica gel
Post, obtains target product, purity 99.58%, yield 61.71%.
Identify this compound, molecular formula C using DEI-MS55H34N4O, detected value [M+1]+=766.59, value of calculation
766.27.
The synthesis of embodiment 7 compound 29
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, addition 0.01mol 5- (9- (4- bromophenyl) -9- carbazole -
3- yl) -10- phenyl -5,10- dihydrophenazine, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2
(dba)3, 1 × 10-4Mol tri-butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is completely, naturally cold
But, filter, filtrate revolving, cross silicagel column, obtain target product, purity 99.52%, yield 65.71%.
Identify this compound, molecular formula C using DEI-MS49H32N4O, detected value [M+1]+=692.56, value of calculation
692.26.
The synthesis of embodiment 8 compound 35
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol 3,6- bis- (phenazinyl) -9- (4- bromine
Phenyl) carbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The tertiary fourth of mol tri-
Base phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filters, filtrate revolving, cross silica gel
Post, obtains target product, purity 99.62%, yield 62.71%.
Identify this compound, molecular formula C using DEI-MS55H34N4O3, detected value [M+1]+=798.59, value of calculation
798.26.
The synthesis of embodiment 9 compound 42
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol3,6- bis- (hexichol amido) -9- (4 '-bromine
Xenyl) carbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri- uncle
Butyl phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filters, filtrate revolving, cross silicon
Glue post, obtains target product, purity 99.52%, yield 61.71%.
Identify this compound, molecular formula C using DEI-MS61H42N4O, detected value [M+1]+=846.62, value of calculation
846.34.
The synthesis of embodiment 10 compound 45
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under the atmosphere being passed through nitrogen, adds 0.01mol3,6- bis- (phenoselenazine base) -9- (4- bromine
Phenyl) carbazole, 0.025mol acridone, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The tertiary fourth of mol tri-
Base phosphine, 150ml toluene, it is heated to reflux 24 hours, sample point plate, reaction is complete, natural cooling, filters, filtrate revolving, cross silica gel
Post, obtains target product, purity 99.62%, yield 63.61%.
Identify this compound, molecular formula C using DEI-MS55H34N4OSe2, detected value [M+1]+=926.41, value of calculation
926.11.
The compounds of this invention can use as emitting layer material, to the compounds of this invention 4, compound 13 and current material
CBP carries out the test of hot property, luminescent spectrum and HOMO, lumo energy, and testing result is as shown in table 1.
Table 1
Note：Thermal weight loss temperature Td is in nitrogen atmosphere weightless 1% temperature, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, open up Pu Kang using Japan
SR-3 spectroradiometer measures；Φ f is the solid powder fluorescence quantum efficiency (Maya2000Pro using U.S.'s marine optics
Fiber spectrometer, the test solid fluorescence amount of the C-701 integrating sphere of Lan Fei company of the U.S. and marine optics LLS-LED light source composition
Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method is measured)；Highest occupied molecular rail
Road HOMO energy level and minimum occupied molecular orbital lumo energy are to be divided by photoelectron emissions spectrometer (AC-2 type PESA), UV, visible light
Light photometric determination, tests as atmospheric environment.
From upper table data, the compounds of this invention has suitable HOMO, lumo energy and higher heat stability,
It is suitable as the material of main part of luminescent layer；Meanwhile, the compounds of this invention has suitable luminescent spectrum, and higher Φ f is so that answer
Got a promotion as the OLED efficiency of dopant material and life-span with the compounds of this invention.
The compound describing present invention synthesis in detail below by way of device embodiments 11-20 and comparative example 1 is made in the devices
Application effect for luminescent layer material of main part., compared with embodiment 11, the processing technology of described device is complete for device embodiments 12-20
Exactly the same, and employed identical baseplate material and electrode material, the thickness of electrode material is also consistent, different
It is that in device, emitting layer material there occurs change.Device embodiments 11-20 compared with comparative example 1, device described in comparative example 1 send out
Light layer material uses existing conventional raw material, and the device emitting layer material of device embodiments 11-20 uses the present invention
Compound.The structure composition of each embodiment obtained device is as shown in table 2.The performance test results of each device are as shown in table 3.
Device embodiments 11
Transparent substrate layer 1/ITO anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4
(compound 2 and GD-19 are according to 100 for (TAPC, thickness 80nm)/luminescent layer 5：5 weight is than blending, thickness 30nm)/electronics biography
Defeated layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).Each associated materials
Structural formula as follows：
Concrete preparation process is as follows：
Ito anode layer 2 (thickness is 150nm) is washed, carry out neutralizing treatment, pure water successively, be dried after again
Carry out ultraviolet-ozone to wash to remove the organic residue on transparent ITO surface.
On the ito anode layer 2 having carried out after above-mentioned washing, using vacuum deposition apparatus, being deposited with thickness is 10nm's
Molybdenum trioxide MoO3Use as hole injection layer 3.And then the TAPC of evaporation 80nm thickness is as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, make the luminescent layer 5 of OLED luminescent device, its structure includes OLED and sends out
As material of main part, as dopant material, dopant material doping ratio is 5% weight to GD-19 to the used material compound 2 of photosphere 5
Amount ratio, luminescent layer thickness is 30nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are TPBI.The vacuum evaporation coating of this material
Thick is 40nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, make lithium fluoride (LiF) layer that thickness is 1nm, this layer is
Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminum (Al) layer that thickness is 80nm, this layer is negative electrode
Reflection electrode layer 8 uses.
After OLED luminescent device accomplished as described above, with known drive circuit, anode and negative electrode are coupled together, survey
The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.The test knot of made OLED luminescent device
Fruit is shown in Table 3.
Table 2
Table 3
| Device code name | Current efficiency | Color | The LT95 life-span |
| Embodiment 11 | 1.8 | Green glow | 3.4 |
| Embodiment 12 | 1.9 | Green glow | 4.3 |
| Embodiment 13 | 1.6 | Green glow | 3.6 |
| Embodiment 14 | 1.5 | Green glow | 2.6 |
| Embodiment 15 | 1.5 | Green glow | 3.6 |
| Embodiment 16 | 1.8 | Green glow | 2.2 |
| Embodiment 17 | 1.9 | Green glow | 3.9 |
| Embodiment 18 | 2.0 | Green glow | 2.2 |
| Embodiment 19 | 1.9 | Green glow | 4.9 |
| Embodiment 20 | 1.6 | Green glow | 3.0 |
| Comparative example 1 | 1.0 | Green glow | 1.0 |
Explanation:Using comparative example 1 as reference, comparative example 1 device property indices are set to 1.0 to device detection performance.Than
It is 6.5cd/A (@10mA/cm compared with the current efficiency of example 12)；CIE chromaticity coordinates is (0.32,0.61)；The LT95 life-span under 5000 brightness
Decay to 3.8Hr.Life-span test system is the OLED life test of owner of the present invention and Shanghai University's joint research
Instrument.
The compound conduct in the devices of present invention synthesis is described below by way of device embodiments 21-25 and comparative example 2
The application effect of photosphere dopant material.Device embodiments 21-25 of the present invention, comparative example 2 institute compared with device embodiments 11
The processing technology stating device is identical, and employed identical baseplate material and electrode material, the thickness of electrode material
Also it is consistent, except that converting to the emitting layer material in device, doping content is 7%.Each embodiment gained
The structure composition of device is as shown in table 4.The performance test results of each device are as shown in table 5.
Table 4
Table 5
| Device code name | Current efficiency | Color | The LT95 life-span |
| Embodiment 21 | 1.8 | Green glow | 3.6 |
| Embodiment 22 | 2.0 | Green glow | 3.0 |
| Embodiment 23 | 1.9 | Green glow | 3.9 |
| Embodiment 24 | 1.8 | Green glow | 2.8 |
| Embodiment 25 | 2.1 | Green glow | 4.0 |
| Comparative example 2 | 1.0 | Green glow | 1.0 |
Explanation:Using comparative example 2 as reference, comparative example 2 device property indices are set to 1.0 to device detection performance.Than
It is 9.5cd/A (@10mA/cm compared with the current efficiency of example 22)；CIE chromaticity coordinates is (0.27,0.65)；The LT95 life-span under 5000 brightness
Decay to 8.2Hr.Life-span test system is the OLED life test of owner of the present invention and Shanghai University's joint research
Instrument.
The result of table 3 can be seen that compound of the present invention can be applied and OLED luminous organ as luminescent layer material of main part
Part makes, and compared with comparative example 1, either efficiency or life-span all ratio known OLED material larger changes of acquisition, especially
It is the larger lifting of the driving life-span acquisition of device.
The result of table 5 can be seen that compound of the present invention can be applied and OLED luminous organ as luminescent layer dopant material
Part makes, and compared with comparative example 2, either efficiency or life-span all ratio known OLED material larger changes of acquisition, especially
It is the larger lifting of the driving life-span acquisition of device.
In order to compare the different components situation that efficiency decays at higher current densities, define efficiency attenuation quotientCarry out table
Show, it represents that driving current is 100mA/cm2When maximal efficiency μ 100 of device and the difference of maximal efficiency μm of device with maximum
Ratio between efficiency,Value is bigger, illustrates that the efficiency roll-off of device is more serious, conversely, explanation device is fast at higher current densities
The decline problem of fall of speed is under control.
The compounds of this invention can use as emitting layer material, to the compounds of this invention 4 (device embodiments 22), chemical combination
Thing 35 (device embodiments 18), compound 45 (device embodiments 20) and current material CBP prepare device and enter line efficiency respectively and decline
Subtract coefficientMensure, testing result is as shown in table 6.
Table 6
From the point of view of data above application, the compounds of this invention has well as emitting layer material in OLED luminescent device
Application effect, there is good industrialization prospect.
Although the present invention has been disclosed by embodiment and preferred implementation it should be appreciated that the invention is not restricted to institute's public affairs
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
The scope of attached claim should arrangement to cover all such modifications and be similar to consistent with explanation the widest.
Claims (7)
1. a kind of compound with acridone as core is it is characterised in that described compound structure such as formula (1) is shown：
In formula (1), Ar is expressed as-Ar1- R or-R；Wherein, Ar1Represent phenyl, dibiphenylyl, terphenyl or naphthyl；
R chooses formula (2) or structure shown in formula (3)：
Wherein, Ar2Represent phenyl, C1-10Phenyl, dibiphenylyl, terphenyl, naphthyl or anthracene that straight or branched alkyl replaces
Base；R1、R2、R3Independently choose carbon atom be the alkyl of 1-10, carbon atom be 4-20 without heteroatomic aromatic radical,
Formula (4), formula (5), formula (6) or structure shown in formula (7)；R2、R3It is asynchronously hydrogen；
Ar3、Ar4、Ar5Expression C independently1-10The substituted or unsubstituted phenyl of straight or branched alkyl, dibiphenylyl, three
Phenyl, naphthyl or anthryl；X1It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of straight or branched alkyl replacement,
One of tertiary amine groups that the alkylidene of aryl replacement, alkyl or aryl replace.
2. compound according to claim 1 is it is characterised in that R3It is expressed as shown in formula (4), formula (6) or formula (7)
During structure, R2It is expressed as hydrogen atom.
3. compound according to claim 1 it is characterised in that in formula (1) R be：
In any one.
4. compound according to claim 1 is it is characterised in that the concrete structure formula of described compound is：
In any one.
5. a kind of luminescent device comprising compound described in any one of Claims 1 to 4 is it is characterised in that described compound conduct
The material of main part of luminescent layer, for making OLED.
6. a kind of luminescent device comprising compound described in any one of Claims 1 to 4 is it is characterised in that described compound conduct
The dopant material of luminescent layer, for making OLED.
7. a kind of method preparing compound described in any one of Claims 1 to 4 is it is characterised in that reaction side in preparation process
Formula is：
Specifically preparation process is：
Take Ar-Br and acridone, dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, sodium tert-butoxide；In inert atmosphere
Under, the mixed solution of above-mentioned reactant is reacted 10～24 hours at 95～110 DEG C of temperature, then cools down and filter reaction molten
Liquid, filtrate revolving, cross silicagel column, obtain target product；
Described Ar-Br is 1 with the mol ratio of acridone:2.0～3.0, Pd2(dba)3With the mol ratio of Ar-Br be 0.006～
0.02:1, tri-butyl phosphine is 0.006～0.02 with the mol ratio of Ar-Br:1, sodium tert-butoxide is 1.0 with the mol ratio of Ar-Br
～3.0:1.
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| CN107057682A (en) * | 2016-04-25 | 2017-08-18 | 中节能万润股份有限公司 | A kind of compound as core using acridone and its application on organic electroluminescence device |
| CN109369652A (en) * | 2018-11-15 | 2019-02-22 | 武汉华星光电半导体显示技术有限公司 | A kind of blue light thermal activation delayed fluorescence material and its application |
| KR20200137150A (en) * | 2019-05-29 | 2020-12-09 | 성균관대학교산학협력단 | Organic phosphorescent light emitting compound at room temperature, and organic light emitting device having the organic phosphorescent light emitting compound |
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| CN104529940A (en) * | 2014-12-15 | 2015-04-22 | 吉林奥来德光电材料股份有限公司 | Phenothiazine dioxide derivative, preparation method and organic luminescent device |
| CN104813496A (en) * | 2012-11-30 | 2015-07-29 | 默克专利有限公司 | Electronic device |
| KR20150088163A (en) * | 2014-01-22 | 2015-07-31 | 주식회사 엠비케이 | New organic electroluminescent compounds and organic electroluminescent device comprising the same |
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| US20090153030A1 (en) * | 2007-12-14 | 2009-06-18 | Shouquan Huo | Oled device with substituted acridone compounds |
| CN104813496A (en) * | 2012-11-30 | 2015-07-29 | 默克专利有限公司 | Electronic device |
| KR20150088163A (en) * | 2014-01-22 | 2015-07-31 | 주식회사 엠비케이 | New organic electroluminescent compounds and organic electroluminescent device comprising the same |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107057682A (en) * | 2016-04-25 | 2017-08-18 | 中节能万润股份有限公司 | A kind of compound as core using acridone and its application on organic electroluminescence device |
| CN109369652A (en) * | 2018-11-15 | 2019-02-22 | 武汉华星光电半导体显示技术有限公司 | A kind of blue light thermal activation delayed fluorescence material and its application |
| KR20200137150A (en) * | 2019-05-29 | 2020-12-09 | 성균관대학교산학협력단 | Organic phosphorescent light emitting compound at room temperature, and organic light emitting device having the organic phosphorescent light emitting compound |
| KR102304294B1 (en) * | 2019-05-29 | 2021-09-23 | 성균관대학교산학협력단 | Organic phosphorescent light emitting compound at room temperature, and organic light emitting device having the organic phosphorescent light emitting compound |
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