CN107068876B - A kind of organic electroluminescence device and its application based on 10,10- diaryl anthracene ketone compound - Google Patents
A kind of organic electroluminescence device and its application based on 10,10- diaryl anthracene ketone compound Download PDFInfo
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Abstract
The invention discloses one kind to contain 10, the organic electroluminescence device of 10- diaryl anthracene ketone compound and its application, the device includes hole transmission layer, luminescent layer, electron transfer layer, the device emitting layer material contains with 10,10- diaryl anthrone is the compound of core group, shown in the structural formula of the compound such as general formula (1).The present invention is with 10,10- diaryl anthrone is the material of core group because having lesser triplet state and singlet energy difference, therefore it is easily achieved energy transmission between Subjective and Objective material, the energy to scatter and disappear in the form of heat originally is set to be easily obtained utilization, to be easier to obtain the high efficiency of device, further, when dopant material is selected as fluorescent material, it is easier to obtain the luminous radiation of dopant material, to be easier to obtain the long-life of material.
Description
Technical field
The present invention relates to technical field of semiconductors, are with 10,10- diaryl anthrone more particularly, to a kind of emitting layer material
Organic electroluminescence device and its application for the compound of core.
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 be clipped in Different electrodes film layer it
Between organic functional material, various different function materials are overlapped mutually depending on the application collectively constitutes OLED luminescent device together.
As current device, when the two end electrodes application 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 further compound in luminescent layer, i.e. generation OLED electroluminescent.
Application of the Organic Light Emitting Diode (OLED) in terms of large-area flat-plate is shown and is illuminated causes industry and
The extensive concern of art circle.However, traditional organic fluorescence materials can only be shone using 25% singlet exciton to be formed is electrically excited, device
The internal quantum efficiency of part is lower (up to 25%).External quantum efficiency is generally lower than 5%, and there are also very big with the efficiency of phosphorescent devices
Gap.Although phosphor material can efficiently use electricity since the strong SO coupling in heavy atom center enhances intersystem crossing
The singlet exciton formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material exists
Expensive, stability of material is poor, and device efficiency tumbles the problems such as serious and limits it in the application of OLEDs.Hot activation is prolonged
Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.It should
Class material generally has poor (the △ E of small singlet-tripletST), triplet excitons can be changed by anti-intersystem crossing
It shines at singlet exciton.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation, device it is interior
Quantum efficiency can achieve 100%.Meanwhile material structure is controllable, and property is stablized, and it is cheap to be not necessarily to precious metal, in OLED
Field has a extensive future.
Although theoretically 100% exciton utilization rate may be implemented in TADF material, following problem there are in fact:
(1) T1 the and S1 state for designing molecule has strong CT feature, very small S1-T1 state energy gap, although can pass through
TADF process realizes high T1→S1State exciton conversion ratio, but low S1 state radiation transistion rate is also resulted in, consequently it is difficult to have both
(or realizing simultaneously) high exciton utilization rate and high fluorescent radiation efficiency；
(2) even if doping device has been used to mitigate T exciton concentration quenching effect, the device of most of TADF materials is in height
Efficiency roll-off is serious under current density.
For current OLED shows the actual demand of Lighting Industry, the development of OLED material is also far from enough at present, falls
Afterwards in the requirement of panel manufacturing enterprise, the exploitation of the organic functional material as material enterprise development higher performance seems especially heavy
It wants.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the present invention provides one kind to be based on 10,10- diaryl anthracene ketone compound
Organic electroluminescence device.The present invention is based on TADF mechanism using 10,10- diaryl anthrone be the compound of core as hair
Photosphere material is applied on Organic Light Emitting Diode, has good photoelectric properties, can satisfy OLED device enterprise, especially
The demand of OLED display panel and OLED Illumination Enterprise.
Technical scheme is as follows:
One kind being based on the organic electroluminescence device of 10,10- diaryl anthracene ketone compound, which includes hole transport
Layer, luminescent layer, electron transfer layer, the device emitting layer material contain the chemical combination with 10,10- diaryl anthrone for core group
Object, shown in the structural formula of the compound such as general formula (1):
In general formula (1), R is expressed as general formula (2), general formula (3), structure shown in general formula (4) or general formula (5):
Wherein, X1For oxygen atom, sulphur atom, C1-10The alkylene of alkylidene, aryl substitution that linear or branched alkyl group replaces
One of the amido that base, alkyl or aryl replace；
R1Indicate phenyl, xenyl, naphthalene, anthryl or phenanthryl；
R2、R3Structure shown in selection hydrogen independently, general formula (6) or general formula (7)；
A isX2、X3It is expressed as oxygen atom, sulphur atom, C1-10What linear or branched alkyl group replaced
One of the amido that alkylidene, the alkylidene of aryl substitution, alkyl or aryl replace；
General formula (6), general formula (7) and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3
Key, CL‘3-CL’4Key or CL‘4-CL’5Key connection.
When a is indicatedAnd and CL4-CL5Key or CL‘4-CL’5When key connection, X1And X2Position overlapping, only take X1Or
X2；X3For oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the alkane of alkylidene, aryl substitution that linear or branched alkyl group replaces
One of the amido that base or aryl replace.
R is indicated in the general formula (1):
Any one of.
The concrete structure formula of the compound based on 10,10- diaryl anthrone are as follows:
Material of main part of the material as luminescent layer shown in the general formula (1)；The dopant material of the luminescent layer is under use
One of column general formula (8), (9), (10), material shown in (11):
In general formula (8), B1-B10 is selected as hydrogen, C1-30Linear or branched alkyl group replace alkyl or alkoxy, replace or
Unsubstituted C6-30Aryl, it is substituted or unsubstituted 3 yuan to 30 unit's heteroaryls；B1-B10 is not hydrogen simultaneously；
In general formula (9), Y1-Y6 one kind independent for being expressed as oxygen, carbon, nitrogen-atoms； It is expressed as containing there are two the groups of atom to pass through the connected cyclization of any chemical bond；
Y1~Y4 one kind independent for being expressed as oxygen, carbon, nitrogen-atoms in general formula (10), general formula (11)；It is expressed as being connected to containing the group there are two atom by any chemical bond
Ring.
The material of the hole transmission layer is the compound containing triarylamine group, and the structural formula general formula of the compound is such as
Shown in general formula (12):
D1-D3 respectively independently indicates substituted or unsubstituted C in general formula (12)6-30Aryl, it is substituted or unsubstituted 3 yuan extremely
30 unit's heteroaryls；D1-D3 can be same or different.
The material of the electron transfer layer is general formula (13), (14), (15), (16), one in material shown in (17)
Kind:
General formula (13), general formula (14), general formula (15), general formula (16), E1-E10 is selected as hydrogen, C in general formula (17)1-30Straight chain
Or alkyl or alkoxy, substituted or unsubstituted C that branched alkyl replaces6-30Aryl, substituted or unsubstituted 3 yuan to 30 yuan it is miscellaneous
Aryl；E1-E10 is not hydrogen simultaneously.
The luminescent device further includes hole injection layer；The hole injection layer material be having structure general formula (18),
(19), one of material shown in (20):
In general formula (18), F1-F3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan substituted or unsubstituted
To 30 unit's heteroaryls；F1-F3 can be same or different；
In general formula (19), general formula (20), G1-G6 expression hydrogen atom independent, itrile group, halogen, amide groups, alcoxyl
Base, ester group, nitro, C1-30Carbon atom, the substituted or unsubstituted C of linear or branched alkyl group substitution6-30Aryl, 3 yuan to 30 yuan it is miscellaneous
Aryl；G1-G6 is not hydrogen simultaneously.
The luminescent device further includes electron injecting layer；The electron injecting layer material is one in lithium, lithium salts or cesium salt
Kind；The lithium salts is 8-hydroxyquinoline lithium, lithium fluoride, lithium carbonate, Lithium Azide；The cesium salt is cesium fluoride, cesium carbonate, nitrine
Change caesium.
Compound shown in the general formula (1) can also be used as the dopant material of luminescent layer.
The mass ratio of the material of main part of the dopant material and luminescent layer of the luminescent layer is 0.005~0.2:1.
A kind of application of the organic electroluminescence device, the organic electroluminescence device are used to prepare top-illuminating OLED
Luminescent device.
A kind of application of the organic electroluminescence device, the organic electroluminescence device are applied to AM-OLED and show
Device.
The present invention is beneficial to be had the technical effect that
The ketone compounds of diaryl anthracene containing 10,10- for forming OLED luminescent device of the present invention have the structure of TADF
Feature, very small S1-T1 state energy gap easy to accomplish is poor, in excitation, the anti-system of triplet state easy to accomplish to singlet
Between alter more, make originally cannot shine, dispersed heat is converted into the energy that can produce luminous energy in the form of heat, and be expected to obtain pole
High efficiency.
It is analyzed based on principles above, OLED luminescent device of the present invention, both can choose fluorescent material as doping material
Material, also can choose phosphor material as dopant material, can also be by TADF material of the present invention directly as dopant material
It uses.
It is described with 10,10- diaryl anthrone be core compound as OLED luminescent device material of main part collocation iridium,
Platinum class phosphor material or anthracene class fluorescent material in use, device current efficiency, power efficiency and external quantum efficiency obtain very
It is big to improve；Meanwhile device lifetime is promoted clearly.Further, on OLED device layer structure matching, hole is introduced
After electron injecting layer, keep transparent anode, metallic cathode and organic material contact interface more stable, hole, electron injection effect
It is promoted；Hole transmission layer again can lamination be two or more layers, the hole transmission layer of adjacent luminescent layer side can be named as electricity again
Sub- barrier layer (EBL) provides electronic blocking effect, promotes exciton combined efficiency in luminescent layer, adjacent hole injection layer side
Hole transmission layer then play the role of hole transport and reduce exciton transfer barrier；Electron transfer layer again can lamination be two layers or
The electron transfer layer of multilayer, adjacent luminescent layer side can be named as hole blocking layer (HBL) again, provide hole barrier effect,
Promote exciton combined efficiency in luminescent layer, the electron transfer layer of adjacent electron injecting layer side then plays electron-transport and reduction
The effect of exciton transfer barrier.It should be mentioned, however, that each of these layers are not necessarily present.
The combined effect of OLED device compound of the present invention: so that the driving voltage of device reduces, current efficiency, function
Rate efficiency, external quantum efficiency are further enhanced, and it is obvious that device lifetime promotes effect.Have in OLED luminescent device good
Application effect, have good industrialization prospect.
Make us against expectation, it has been found that, the compound combination being more particularly described hereinafter realizes this purpose,
And lead to the improvement of organic electroluminescence device, especially voltage, efficiency and the improvement in service life.This especially suitable for red or
The electroluminescent device of green phosphorescent, especially when using device architecture and combination of materials of the invention, situation is such.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of stacked OLED device of the embodiment of the present invention；
In Fig. 1: 1 be transparent substrates, 2 be ito anode layer, 3 be hole injection layer (HIL), 4 be hole transmission layer (HTL),
5 be electronic barrier layer (EBL), 6 be luminescent layer (EML), 7 be hole blocking layer (HBL), 8 be electron transfer layer (ETL), 9 be electricity
Sub- implanted layer (EIL), 10 are cathode reflection electrode layer.
Fig. 2 is the structural formula of critical materials used in device embodiments of the present invention.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of 1 raw material A of embodiment
In 1L there-necked flask, it is added 19.8g phenol (0.21mol), 20.8g anthraquinone (0.10mol), 0.2g mercaptopropionic acid,
400mL dichloroethanes is mixed, is warming up to 60~65 DEG C of dropwise addition 3.0g methanesulfonic acids, is added dropwise, and at 60~65 DEG C, protects
Temperature reaction 4 hours；After reaction, cooling washing liquid separation, organic phase removed under reduced pressure solvent obtain crude product, are tied again with dehydrated alcohol
Crystalline substance, column chromatograph to obtain white crystal-compound X, HPLC purity 99.5%, yield 46.58%；
18.9g compound X (0.05mol) is added in 500mL three-necked flask, 100g pyridine is cooled to 0~5 DEG C of dropwise addition
33.8g trifluoromethanesulfanhydride anhydride (0.12mol) reacts at room temperature 6 hours；Then plus water quenching is gone out, and extracts liquid separation, organic phase removed under reduced pressure
Solvent, column chromatograph to obtain raw material A, HPLC purity 99.7%, yield 74.88%；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C28H16F6O7S2, theoretical value: 642.0242, test value:
642.0248。
Elemental analysis (C28H16F6O7S2): theoretical value C:52.34, H:2.51, O:17.43, test value: C52.38, H:
2.52, O:17.46.
The synthesis of 2 raw material B of embodiment
It in 250ml there-necked flask, under nitrogen protection, is added 6.42g raw material A (0.01mol), where is 10.16g duplex boric acid frequency
Alcohol ester (0.04mol), 4.90g potassium acetate (0.05mol), 0.30g pd2 (dba) 3,0.20g tri-tert phosphorus, 100ml toluene,
Back flow reaction 20 hours；After reaction, cooling, filtering, filtrate rotates, and column chromatographs to obtain raw material B, HPLC purity 99.8%, receives
Rate 88.26%；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C38H40B2O5, theoretical value: 598.3062, test value:
598.3066。
Elemental analysis (C38H40B2O5): theoretical value C:76.28, H:6.74, O:13.37, test value C:76.26, H:
6.75, O:13.40.
The synthesis of 3 compound 1 of embodiment
Synthetic route:
In 250ml there-necked flask, under nitrogen protection, it is added 3.21g raw material A (0.005mol), 2.20g compound M01
(0.012mol), 1.44g sodium tert-butoxide (0.015mol), 0.15g pd2 (dba) 3,0.10g tri-tert phosphorus, 100ml toluene,
Back flow reaction 20 hours；After reaction, cooling, filtering, filtrate revolving, column chromatographs to obtain compound 1, HPLC purity 99.9%,
Yield 78.40%；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C50H32N2O3, theoretical value: 708.2413, test value:
708.2411。
Elemental analysis (C50H32N2O3): theoretical value C:84.73, H:4.55, N:3.95, O:6.77, test value C:
84.71, H:4.55, N:3.98, O:6.76.
The synthesis of 4 compound 3 of embodiment
Synthetic route:
By the synthetic method preparation of compound 1 in embodiment 3, difference is to replace M01 with M02；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C56H44N2O, theoretical value: 760.3454, test value:
760.3458。
Elemental analysis (C56H44N2O): theoretical value C:88.39, H:5.83, N:3.68, O:2.10, test value C:88.36,
H:5.85, N:3.67, O:2.12.
The synthesis of 5 compound 5 of embodiment
Synthetic route:
By the synthetic method preparation of compound 1 in embodiment 3, difference is to replace M01 with M03；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C58H36N2O, theoretical value: 776.2828, test value:
776.2824。
Elemental analysis (C58H36N2O): theoretical value C:89.66, H:4.67, N:3.61, O:2.06, test value C:89.62,
H:4.68, N:3.60, O:2.10.
The synthesis of 6 compound 10 of embodiment
Synthetic route:
By the synthetic method preparation of compound 1 in embodiment 3, difference is to replace M01 with M04；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C68H48N2O, theoretical value: 908.3767, test value:
908.3764。
Elemental analysis (C68H48N2O): theoretical value C:89.84, H:5.32, N:3.08, O:1.76, test value C:89.86,
H:5.35, N:3.05, O:1.74.
The synthesis of 7 compound 15 of embodiment
Synthetic route:
By the synthetic method preparation of compound 1 in embodiment 3, difference is to replace M01 with M05；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C62H36N2O3, theoretical value: 856.2726, test value:
856.2722。
Elemental analysis (C62H36N2O3): theoretical value C:86.90, H:4.23, N:3.27, O:5.60, test value C:
86.88, H:4.25, N:3.29, O:5.58.
The synthesis of 8 compound 30 of embodiment
Synthetic route:
In 250ml there-necked flask, under nitrogen protection, it is added 2.99g raw material B (0.005mol), 3.87g compound M06
(0.012mol), 1.44g sodium tert-butoxide (0.015mol), 0.15g pd2 (dba) 3,0.10g tri-tert phosphorus, 100ml toluene,
Back flow reaction 20 hours；After reaction, cooling, filtering, filtrate revolving, column chromatographs to obtain compound 30, HPLC purity 99.8%,
Yield 64.33%；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C62H40N2O, theoretical value: 828.3141, test value:
828.3144。
Elemental analysis (C62H40N2O): theoretical value C:89.83, H:4.86, N:3.38, O:1.93, test value C:89.86,
H:4.86, N:3.35, O:1.93.
The synthesis of 9 compound 34 of embodiment
Synthetic route:
By the synthetic method preparation of compound 30 in embodiment 8, difference is to replace M06 with M07；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C68H52N2O, theoretical value: 912.4080, test value:
912.4077。
Elemental analysis (C68H52N2O): theoretical value C:89.44, H:5.74, N:3.07, O:1.75, test value C:89.47,
H:5.72, N:3.09, O:1.72.
The synthesis of 10 compound 36 of embodiment
Synthetic route:
By the synthetic method preparation of compound 1 in embodiment 3, difference is to replace M01 with M08；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C68H48N2O3, theoretical value: 940.3665, test value:
940.3662。
Elemental analysis (C68H48N2O3): theoretical value C:86.78, H:5.14, N:2.98, O:5.10, test value C:
86.75, H:5.12, N:3.00, O:5.13.
The synthesis of 11 compound 49 of embodiment
Synthetic route:
By the synthetic method preparation of compound 1 in embodiment 3, difference is to replace M01 with M09；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C62H42N4O, theoretical value: 858.3359, test value:
858.3352。
Elemental analysis (C62H42N4O): theoretical value C:86.69, H:4.93, N:6.52, O:1.86, test value C:86.67,
H:4.95, N:6.55, O:1.83.
The synthesis of 12 compound 62 of embodiment
Synthetic route:
By the synthetic method preparation of compound 1 in embodiment 3, difference is to replace M01 with M10；
The source high resolution mass spectrum ESI, positive ion mode, molecular formula C62H38N4O3, theoretical value: 886.2944, test value:
886.2941。
Elemental analysis (C62H38N4O3): theoretical value C:83.95, H:4.32, N:6.32, O:5.41, test value C:
83.93, H:4.30, N:6.35, O:5.42.
The compounds of this invention can be used as emitting layer material use, to the compounds of this invention 42, compound 68, current material
CBP, current material BD1 carry out the test of hot property, luminescent spectrum, fluorescence quantum efficiency and cyclic voltammetric stability, detection
The results are shown in Table 1.
Table 1
| Compound | Tg(℃) | Td(℃) | λPL(nm) | Φf | Cyclic voltammetric stability |
| Compound 42 | 152 | 421 | 461 | 85.6 | It is excellent |
| Material C BP | 113 | 353 | 369 | 26.1 | Difference |
| Compound 68 | 148 | 435 | 452 | 88.2 | It is excellent |
| Material BD1 | - | 334 | 486 | 28.3 | Difference |
Note: glass transition temperature Tg is by differential scanning calorimetry (DSC, German Nai Chi company DSC204F1 differential scanning calorimetry
Instrument) measurement, 10 DEG C/min of heating rate；Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, public in Japanese Shimadzu
It is measured on the TGA-50H thermogravimetric analyzer of department, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths,
General health SR-3 spectroradiometer is opened up using Japan to measure；Φ f is that solid powder fluorescence quantum efficiency (utilizes U.S.'s marine optics
Maya2000Pro fiber spectrometer, Lan Fei company of the U.S. C-701 integrating sphere and marine optics LLS-LED light source composition
Solid fluorescence quantum efficiency test system, reference literature Adv.Mater.1997 are tested, 9,230-232 method is measured).
Cyclic voltammetric stability is identified by the redox characteristic of cyclic voltammetry test material；Test-strips
Part: test sample is dissolved in the methylene chloride and acetonitrile mixed solvent that volume ratio is 2:1, and concentration 1mg/mL, electrolyte is 0.1M
The organic solution of tetrabutyl ammonium tetrafluoroborate or hexafluorophosphate.Reference electrode is Ag/Ag+ electrode, is titanium to electrode
Plate, working electrode are ITO electrode, and cycle-index is 20 times.
By upper table data it is found that the compounds of this invention has suitable luminescent spectrum, higher Φ f is suitable as shining
Layer material；Meanwhile the compounds of this invention has preferable oxidation-reduction stability, higher thermal stability, so that using this hair
The OLED device efficiency of bright compound and service life get a promotion.
In the devices below by way of device embodiments 1~16 and device comparative example 1 the present invention will be described in detail compound combination
Application effect.The production of device embodiments 2~16, the device compared with device embodiments 1 of device comparative example 1 of the present invention
Technique is identical, and uses identical baseplate material and electrode material, the difference is that device survey stepped construction,
Collocation material and thicknesses of layers are different.Device stack structure is as shown in table 2.The performance test knot of each embodiment obtained device
Fruit is as shown in table 3.
Device embodiments 1
Device stack structure is as shown in device architecture schematic diagram 1: including hole transmission layer 4, luminescent layer 6, electron transfer layer
8。
Ito anode layer 2 (thickness: 150nm)/hole transmission layer 4 (thickness: 120nm, material: HT6)/luminescent layer 6 (thickness:
40nm, material: compound 1 and GD1 are constituted by weight 90:10 blending)/electron transfer layer 8 (thickness: 35nm, material: ET2 and
EI1, mass ratio 1:1)/Al (thickness: 100nm).
Specific preparation process is as follows:
Ito anode layer 2 (film thickness 150nm) is washed, is successively carried out after progress neutralizing treatment, pure water, drying ultraviolet
Line-ozone washing is to remove the organic residue on the transparent surface ITO.
On the ito anode layer 2 after the washing, using vacuum deposition apparatus, hole transmission layer 4, hole transport is deposited
Layer material uses HT6, and film thickness 120nm, this layer is as the hole transmission layer 4 in device architecture；
On hole transmission layer 4, by vacuum evaporation mode, luminescent layer 6 is deposited, emitting layer material is made using compound 1
Based on material, for GD1 as dopant material, doping mass ratio is 90:10, and luminescent layer film thickness is 40nm, this layer is as device
Luminescent layer 6 in structure；
On luminescent layer 6, by vacuum evaporation mode, be deposited electron transfer layer 8, electron transport layer materials using ET2 and
EI1 mixing and doping, doping mass ratio are 1:1, and film thickness 35nm, this layer is as the electron transfer layer 8 in device architecture；
On electron transfer layer 8, by vacuum evaporation mode, evaporation cathode aluminium layer, film thickness 100nm, this layer is cathode
Reflection electrode layer 10 uses.
After completing the production of OLED luminescent device as described above, anode and cathode is connected with well known driving circuit
Come, the luminous efficiency of measurement device, the I-E characteristic of luminescent spectrum and device.
Device embodiments 2
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, luminescent layer 6
With electron transfer layer 8.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 110nm, material: HT2)/luminescent layer 6 (thickness: 40nm, material: compound 3 and GD2 are constituted by weight 88:12 blending)/
Electron transfer layer 8 (thickness: 35nm, material: ET02 and EI1, mass ratio 1:1)/Al (thickness: 100nm).
Device embodiments 3
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, luminescent layer
6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI2)/hole transmission layer 4 is (thick
Degree: 110nm, material: HT4)/luminescent layer 6 (thickness: 40nm, material: compound 5 and GD2 are constituted by weight 88:12 blending)/
Electron transfer layer 8 (thickness: 35nm, material: ET3 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 1nm, material:
LiN3)/Al (thickness: 100nm).
Device embodiments 4
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6 and electron transfer layer 8.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 90nm, material: HT3)/electronic barrier layer 5 (thickness: 20nm, material: EB2) (thickness: 40nm, material: chemical combination of/luminescent layer 6
Object 10 and GD3 are constituted by weight 89:11 blending)/electron transfer layer 8 (thickness: 35nm, material: ET3 and EI1, mass ratio 1:
1)/Al (thickness: 100nm).
Device embodiments 5
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, luminescent layer
6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI3 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 70nm, material: HT3)/luminescent layer 6 (thickness: 40nm, material: 15 He of compound
GD3 is constituted by weight 89:11 blending)/electron transfer layer 8 (thickness: 35nm, material: ET3)/electron injecting layer 9 (thickness:
1nm, material: Li)/Al (thickness: 100nm).
Device embodiments 6
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, luminescent layer
6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI4 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 70nm, material: HT6)/luminescent layer 6 (thickness: 40nm, material: 24 He of compound
GD4 is constituted by weight 92:8 blending)/electron transfer layer 8 (thickness: 35nm, material: ET4 and EI1, mass ratio 1:1)/electronics
Implanted layer 9 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
Device embodiments 7
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 90nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB1) (thickness: 40nm, material: chemical combination of/luminescent layer 6
Object 30 and GD4 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness: 20nm, material: HB1)/electron transfer layer 8 (thickness
Degree: 15nm, material: ET2 and EI1, mass ratio 1:1)/Al (thickness: 100nm).
Device embodiments 8
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT5)/electronic barrier layer 5 (thickness: 20nm, material: EB3)/
Luminescent layer 6 (thickness: 40nm, material: compound 34 and GD5 are constituted by weight 92:8 blending)/electron transfer layer 8 (thickness:
35nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 1nm, material: Cs2CO3)/Al (thickness:
100nm)。
Device embodiments 9
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
3 layers of (thickness: the 150nm)/hole of ito anode layer 2 injection (thickness: 50nm, material: HI6 and HT4, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 36 and GD6 are constituted by weight 95:5 blending)/electron transfer layer 8 (thickness:
35nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 1nm, material: EI1)/Al (thickness: 100nm).
Device embodiments 10
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 90nm, material: HT3)/electronic barrier layer 5 (thickness: 20nm, material: EB1) (thickness: 40nm, material: chemical combination of/luminescent layer 6
Object 49 and GD5 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness: 25nm, material: HB1)/electron transfer layer 8 (thickness
Degree: 10nm, material: ET5)/electron injecting layer 9 (thickness: 1nm, material: EI1)/Al (thickness: 100nm).
Device embodiments 11
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT6, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 51 and GD4 are constituted by weight 92:8 blending)/hole blocking layer 7 (thickness:
15nm, material: HB1)/electron transfer layer 8 (thickness: 20nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness
Degree: 1nm, material: Li2CO3)/Al (thickness: 100nm).
Device embodiments 12
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, luminescent layer
6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 70nm, material: HT6)/luminescent layer 6 (thickness: 40nm, material: 62 He of compound
GD6 is constituted by weight 95:5 blending)/hole blocking layer 7 (thickness: 15nm, material: HB1)/electron transfer layer 8 (thickness:
20nm, material: ET6)/electron injecting layer 9 (thickness: 1nm, material: CsF)/Al (thickness: 100nm).
Device embodiments 13
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 63 and GD2 are constituted by weight 88:12 blending)/electron transfer layer 8 (thickness:
35nm, material: ET2 and EI1, mass ratio 1:1)/electron injecting layer 9 (thickness: 1nm, material: CsN3)/Al (thickness: 100nm).
Device embodiments 14
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7 and electron transfer layer 8.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT3, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: compound 78, GH2 and GD2 are constituted by weight 60:30:10 blending)/hole blocking layer 7
(thickness 15nm, material: EB2)/electron transfer layer 8 (thickness: 20nm, material: ET2 and EI1, mass ratio 1:1)/Al (thickness:
100nm)。
Device embodiments 15
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6, hole blocking layer 7, electron transfer layer 8 and electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 50nm, material: HI5 and HT6, in mass ratio 5:
95 blendings are constituted)/hole transmission layer 4 (thickness: 50nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB2)/
Luminescent layer 6 (thickness: 40nm, material: GH3 and compound 68 are constituted by weight 88:12 blending)/hole blocking layer 7 (thickness:
25nm, material: HB1)/electron transfer layer 8 (thickness: 10nm, material: ET5)/electron injecting layer 9 (thickness: 1nm, material:
EI1)/Al (thickness: 100nm).
Device embodiments 16
Device stack structure is as shown in device architecture schematic diagram 1: including hole injection layer 3, hole transmission layer 4, electronics resistance
Barrier 5, luminescent layer 6 and electron transfer layer 8.
Ito anode layer 2 (thickness: 150nm)/hole injection layer 3 (thickness: 10nm, material: HI1)/hole transmission layer 4 is (thick
Degree: 90nm, material: HT6)/electronic barrier layer 5 (thickness: 20nm, material: EB1) (thickness: 40nm, material: GH4 of/luminescent layer 6
Constituted with compound 76 by weight 92:8 blending)/electron transfer layer 8 (thickness: 35nm, material: ET3 and EI1, mass ratio 1:
1)/Al (thickness: 100nm).
Device comparative example 1
Device stack structure is as shown in device architecture schematic diagram 1: including hole transmission layer 4, luminescent layer 6, electron transfer layer 8
With electron injecting layer 9.
Ito anode layer 2 (thickness: 150nm)/hole transmission layer 4 (thickness: 120nm, material: HTI)/luminescent layer 6 (thickness:
40nm, material: GH1 and GD1 is constituted by weight 90:10 blending)/electron transfer layer 8 (thickness: 35nm, material: ET1)/electronics
Implanted layer 9 (thickness: 1nm, material: LiF)/Al (thickness: 100nm).
The OLED is characterized by standard method, from current/voltage/luminous density characteristic line that Lambert emission characteristic is presented
It calculates, and the measurement service life.It determines in 1000cd/m2Electroluminescent spectrum under brightness calculates CIEx and y color coordinates, device
Test data is as shown in table 3.
Table 2
Table 3
Note: for device detection performance using comparative example 1 as reference, 1 device performance indexes of comparative example is set as 1.0.Compare
The current efficiency of example 1 is 32.6cd/A (@1000cd/m2)；Driving voltage is 5.6v (@1000cd/m2)；LT95 under 5000 brightness
Life time decay is 3.5Hr.
Table 3 summarizes the OLED device in 1000cd/m2Voltage needed for brightness, the current efficiency reached and electroluminescent hair
The chromaticity coordinates of light spectrum, and in 5000cd/m2LT95 Decay under brightness.1 comparative device comparative example 1 of device embodiments,
Replace luminescent layer material of main part of the invention, and by combination of materials of the invention at laminated device after, device voltage reduces, electric current
Improved efficiency 60%, 11 times of life-span upgrading；Device embodiments 2~13 are by the material adapted of the invention designed and device stack group
It closes, so that device data is further promoted；Such as device embodiments 14, it is of the invention with 10,10- diaryl anthrone for core group
Material as hybrid agent material when, further obtain extraordinary performance data；Such as device embodiments 15,16, sheet
Invention with 10,10- diaryl anthrone be core group material as luminescent layer dopant material in use, equally obtaining very
Good performance data.
To sum up, the foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (13)
1. one kind be based on 10,10- diaryl anthracene ketone compound organic electroluminescence device, the device include hole transmission layer,
Luminescent layer, electron transfer layer, it is characterised in that the device emitting layer material contains with 10,10- diaryl anthrone for core group
Compound, shown in the structural formula of the compound such as general formula (1):
In general formula (1), R is expressed as general formula (2), general formula (3), structure shown in general formula (4) or general formula (5):
Wherein, X1For oxygen atom, sulphur atom, C1-10Alkylidene, the alkane of alkylidene, aryl substitution that linear or branched alkyl group replaces
One of the amido that base or aryl replace；
R1Indicate phenyl, xenyl, naphthalene, anthryl or phenanthryl；
R2、R3Structure shown in selection hydrogen independently, general formula (6) or general formula (7)；
A isOne of；X2、X3It is expressed as oxygen atom, sulphur atom, C1-10Linear or branched alkyl group replaces
Alkylidene, one of the amido that replaces of the aryl alkylidene, the alkyl or aryl that replace；
General formula (6), general formula (7) and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL'1-CL'2Key, CL'2-CL'3Key,
CL'3-CL'4Key or CL'4-CL'5Key connection.
2. organic electroluminescence device according to claim 1, it is characterised in that when a is indicatedAnd and CL4-CL5Key
Or CL'4-CL'5When key connection, X1And X2Position overlapping, only take X1Or X2；X3For oxygen atom, sulphur atom, selenium atom, C1-10Directly
One of the amido that alkylidene, the alkyl or aryl of alkylidene, aryl substitution that chain or branched alkyl replace replace.
3. organic electroluminescence device according to claim 1, it is characterised in that R is indicated in the general formula (1):
Any one of.
4. organic electroluminescence device according to claim 1, it is characterised in that described to be based on 10,10- diaryl anthrone
Compound concrete structure formula are as follows:
Kind.
5. organic electroluminescence device according to claim 1, it is characterised in that material shown in the general formula (1) is as hair
The material of main part of photosphere；The dopant material of the luminescent layer is using in material shown in general formula (8), (9), (10), (11)
One kind:
In general formula (8), B1-B10 is selected as hydrogen, C1-30The alkyl or alkoxy, substituted or unsubstituted that linear or branched alkyl group replaces
C6-30Aryl, it is substituted or unsubstituted 3 yuan one of to 30 unit's heteroaryls；B1-B10 is not hydrogen simultaneously；
In general formula (9), Y1-Y6 one kind independent for being expressed as oxygen, carbon, nitrogen-atoms； It is expressed as containing there are two the groups of atom to pass through the connected cyclization of any chemical bond；
Y1~Y4 one kind independent for being expressed as oxygen, carbon, nitrogen-atoms in general formula (10), general formula (11)；It is expressed as being connected to containing the group there are two atom by any chemical bond
Ring.
6. organic electroluminescence device according to claim 1, it is characterised in that the material of the hole transmission layer be containing
There is the compound of triarylamine group, shown in the structural formula general formula such as general formula (12) of the compound:
D1-D3 respectively independently indicates substituted or unsubstituted C in general formula (12)6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted
One of heteroaryl；D1-D3 can be same or different.
7. organic electroluminescence device according to claim 1, it is characterised in that under the material of the electron transfer layer is
One of column general formula (13), (14), (15), (16), material shown in (17):
General formula (13), general formula (14), general formula (15), general formula (16), E1-E10 is selected as hydrogen, C in general formula (17)1-30Straight chain or branch
The alkyl or alkoxy, substituted or unsubstituted C that alkyl group replaces6-30Aryl, it is substituted or unsubstituted 3 yuan to 30 unit's heteroaryls
One of；E1-E10 is not hydrogen simultaneously.
8. organic electroluminescence device according to claim 1, it is characterised in that the luminescent device further includes hole note
Enter layer；The hole injection layer material is having structure general formula (18), (19), one of material shown in (20):
In general formula (18), F1-F3 respectively independently indicates substituted or unsubstituted C6-30It is aryl, 3 yuan to 30 yuan substituted or unsubstituted
One of heteroaryl；F1-F3 can be same or different；
In general formula (19), general formula (20), G1-G6 expression hydrogen atom independent, itrile group, halogen, amide groups, alkoxy, ester
Base, nitro, C1-30Carbon atom, the substituted or unsubstituted C of linear or branched alkyl group substitution6-30Aryl, 3 yuan to 30 unit's heteroaryls
One of；G1-G6 is not hydrogen simultaneously.
9. organic electroluminescence device according to claim 1, it is characterised in that the luminescent device further includes electronics note
Enter layer；The electron injecting layer material is one of lithium, lithium salts or cesium salt；The lithium salts be 8-hydroxyquinoline lithium, lithium fluoride,
One of lithium carbonate, Lithium Azide；The cesium salt is one of cesium fluoride, cesium carbonate, cesium azide.
10. organic electroluminescence device according to claim 1, it is characterised in that compound shown in the general formula (1) is also
It can be used as the dopant material of luminescent layer.
11. according to organic electroluminescence device described in claim 1, it is characterised in that the dopant material of the luminescent layer and shine
The mass ratio of the material of main part of layer is 0.005~0.2:1.
12. a kind of application of any one of claim 1~11 organic electroluminescence device, it is characterised in that the Organic Electricity
Electroluminescence device is used to prepare top-illuminating OLED luminescent device.
13. a kind of application of any one of claim 1~11 organic electroluminescence device, it is characterised in that the Organic Electricity
Electroluminescence device is applied to AM-OLED display.
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