CN106543205B - A kind of compound containing benzimidazole and its application on OLED - Google Patents
A kind of compound containing benzimidazole and its application on OLED Download PDFInfo
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Abstract
The invention discloses a kind of using benzimidazole skeleton as the compound of core and its application on organic electroluminescence device, the compound is using benzimidazole and ring is core, the class formation is not easy to crystallize, and has the characteristics that good filming, while triplet with higher and thermal stability.The compounds of this invention as OLED luminescent device luminescent layer material of main part in use, device current efficiency, power efficiency and external quantum efficiency are greatly improved；Meanwhile device lifetime is promoted clearly.
Description
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of containing the compound of benzimidazole and its work
The application for being emitting layer material on Organic Light Emitting Diode.
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.
The organic electroluminescence device of excellent combination property in order to obtain needs to design suitable Subjective and Objective material and optimization
Device architecture, luminescent layer material of main part generally comprise hole and/or electron-transport unit, have suitable carrier transport
Can, and its triplet energy level is required to be higher than illuminator, it just can guarantee that triplet exciton is confined to luminescent layer in this way.In addition, being
Realization carrier is efficiently injected to drop low start voltage, and material of main part should also have relative to the suitable of neighbouring organic layer
Energy level.
In recent years, bipolar host material is led because having the hole of balance and electronic carrier stream in electroluminescent device
Domain is attract attention, and the production that gradually moves towards the industrialization.
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 organic functional material as material enterprise development higher performance is particularly important.
Summary of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provide a kind of compound containing benzimidazole and its
Application on organic electroluminescence device.The compounds of this invention is using benzimidazole and ring is core, as luminous layer main body material
Material is applied to Organic Light Emitting Diode, and the device that the present invention makes has good photoelectric properties, can satisfy panel manufacture enterprise
The requirement of industry.
Technical scheme is as follows:
The applicant provides a kind of using benzimidazole and ring is the compound of core skeleton, and the structure of the compound is such as
Shown in general formula (1):
In general formula (1), X1、X2、X3、X4、Y1、Y2、Y3、Y4Independently be expressed as carbon atom or nitrogen-atoms；And X1、
X2、X3、X4At most there is one to be expressed as nitrogen-atoms；Y1、Y2、Y3、Y4At most there is one to be expressed as nitrogen-atoms；X1、X2、X3、X4、Y1、
Y2、Y3、Y4At least one is expressed as nitrogen-atoms；
Z1It is expressed as one of the tertiary amine groups that oxygen atom, sulphur atom, alkyl or aryl replace；
N=0 or 1；M=0 or 1；And m, n are not equal to 1 simultaneously.
Preferably, the structure of the compound is indicated by any one of following general formula:
Wherein, X1、X2、X3、X4、Y1、Y2、Y3、Y4Independently be expressed as carbon atom or nitrogen-atoms；And X1、X2、X3、
X4At most there is one to be expressed as nitrogen-atoms；Y1、Y2、Y3、Y4At most there is one to be expressed as nitrogen-atoms；
R1It is expressed as any one of substitution or unsubstituted phenyl, pyrimidine radicals, xenyl, quinolyl.
It is furthermore preferred that the concrete structure formula of the compound are as follows:
Any one of.
The applicant additionally provides a kind of luminescent device comprising the compound, master of the compound as luminescent layer
Body material, for making organic electroluminescence device.
The applicant additionally provides a kind of method for preparing the compound, the reaction equation occurred in preparation process
Are as follows:
N=0 or 1；M=0 or 1；And m, n are not equal to 1 simultaneously；
X is expressed as one of the tertiary amine groups that oxygen atom, sulphur atom, alkyl or aryl replace；
The preparation method is as follows:
Weigh bromo-derivative, the Ar of benzimidazole and ring1- H is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine, uncle
Sodium butoxide；Under an inert atmosphere, it by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reacts 10~24 hours,
Cooling and filtering reacting solution, filtrate revolving, crosses silicagel column, obtains target product；
The bromo-derivative and Ar of the benzimidazole and ring1- H molar ratio is 1:0.8~2.0:0.8~2.0, Pd2(dba)3With
The molar ratio of the bromo-derivative of benzimidazole and ring is the bromo-derivative of 0.006~0.02:1, tri-tert-butylphosphine and benzimidazole and ring
Molar ratio be 0.006~0.02:1, the molar ratio of sodium tert-butoxide and benzimidazole and the bromo-derivative of ring is 1.0~3.0:1.
The present invention is beneficial to be had the technical effect that
The compounds of this invention is using benzimidazole and ring is parent nucleus, reconnects aromatic heterocycle group, destroys molecular symmetry,
To destroy the crystallinity of molecule, intermolecular aggtegation is avoided, the compound structure intramolecular includes electron donor
The mobility of electrons and holes, drop low start voltage can be improved in the combination of (donor, D) and electron acceptor (acceptor, A),
Parent nucleus benzimidazole and ring triplet energy level with higher, are confined to compound triplet exciton in luminescent layer, improve hair
Light efficiency, the compounds of this invention are suitable as the use of luminescent layer material of main part.
Compound of the present invention can be used as emitting layer material and make applied to OLED luminescent device, as luminous layer main body
Material can obtain good device performance, and current efficiency, power efficiency and the external quantum efficiency of device are greatly improved；
Meanwhile device lifetime is promoted clearly.
Compound-material of the present invention has good application effect in OLED luminescent device, has good industry
Change prospect.
Detailed description of the invention
Fig. 1 is the device architecture schematic diagram using the compounds of this invention；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminous
Layer, 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be cathode reflection electrode layer.
Fig. 2~5 are respectively the effect of visualization figure of compound 14, compound 64, compound 77, compound 106.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The synthesis of 1 compound 3 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol intermediate A, 0.012mol intermediate a,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.90 yield 54.68%.
Elemental analysis structure (molecular formula C41H24N6S): theoretical value C, 77.83；H,3.82；N,13.28；O,5.07；
Test value: C, 77.76；H,3.86；N,13.32；S,5.06.
HPLC-MS: material molecule amount 632.73 surveys molecular weight 632.59.
The synthesis of 2 compound 5 of embodiment
0.01mol intermediate a, 0.012mol intermediate b is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
97.98%, yield 61.20%.
Elemental analysis structure (molecular formula C42H25N5S): theoretical value C, 79.85；H,3.99；N,11.09；O,5.08；
Test value: C, 79.79；H,3.96；N,11.07；S,5.18
HPLC-MS: material molecule amount 631.75 surveys molecular weight 631.83.
The synthesis of 3 compound 14 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol intermediate B, 0.012mol, intermediate b,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
99.0%, yield 63.4%.
Elemental analysis structure (molecular formula C42H25N5S): theoretical value C, 79.85；H,3.99；N,11.09；O,5.08；
Test value: C, 79.76；H,4.01；N,11.14；S,5.09
HPLC-MS: material molecule amount 631.75 surveys molecular weight 631.69.
The synthesis of 4 compound 35 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol intermediate B, 0.012mol, intermediate c,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.7%, yield 58.7%.
Elemental analysis structure (molecular formula C41H24N6S): theoretical value C, 77.83；H,3.82；N,13.28；O,5.07；
Test value: C, 77.79；H,3.88；N,13.31；S,5.02
HPLC-MS: material molecule amount 632.73 surveys molecular weight 632.65.
The synthesis of 5 compound 47 of embodiment
0.01mol intermediate C, 0.012mol intermediate e is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.60%, yield 61.30%.
Elemental analysis structure (molecular formula C41H24N6O): theoretical value C, 79.85；H,3.92；N,13.63；O,2.59；
Test value: C, 79.79；H,3.88；N,13.58；S,2.75
HPLC-MS: material molecule amount 616.67 surveys molecular weight 616.61.
The synthesis of 6 compound 64 of embodiment
0.01mol intermediate C, 0.012mol, intermediate a is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.3%, yield 59.2%.
Elemental analysis structure (molecular formula C41H24N6O): theoretical value C, 79.85；H,3.92；N,13.63；O,2.59；
Test value: C, 79.76；H,3.89；N,13.70；S,2.65
HPLC-MS: material molecule amount 616.67 surveys molecular weight 616.59.
The synthesis of 7 compound 70 of embodiment
0.01mol intermediate C, 0.015mol intermediate d is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 500ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-tert-butylphosphine, 150ml toluene, is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
99.1%, yield 56.7%.
Elemental analysis structure (molecular formula C41H24N6O): theoretical value C, 79.85；H,3.92；N,13.63；O,2.59；
Test value: C, 79.81；H,3.86；N,13.66；S,2.67
HPLC-MS: material molecule amount 616.67 surveys molecular weight 616.57.
The synthesis of 8 compound 77 of embodiment
0.01mol intermediate D, 0.012mol intermediate f is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.80%, yield 58.80%.
Elemental analysis structure (molecular formula C42H25N5O): theoretical value C, 81.93；H,4.09；N,11.37；O,2.60；
Test value: C, 81.88；H,3.98；N,11.43；S,2.71
HPLC-MS: material molecule amount 615.68 surveys molecular weight 615.65.
The synthesis of 9 compound 91 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol intermediate E, 0.012mol intermediate g,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.50%, yield 59.50%.
Elemental analysis structure (molecular formula C48H30N6): theoretical value C, 83.46；H,4.38N,12.17；
Test value: C, 83.50；H,4.36；N,14.15
HPLC-MS: material molecule amount 690.79 surveys molecular weight 690.72.
The synthesis of 10 compound 106 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, addition 0.01mol intermediate E, 0.012mol intermediate f,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.65%, yield 58.20%.
Elemental analysis structure (molecular formula C47H29N7): theoretical value C, 81.60；H,4.23；N,14.17；
Test value: C, 81.58；H,4.18；N,14.24
HPLC-MS: material molecule amount 691.78 surveys molecular weight 691.70.
The synthesis of 11 compound 107 of embodiment
0.01mol intermediate F, 0.012mol intermediate h is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
99.10%, yield 59.8%.
Elemental analysis structure (molecular formula C47H29N7): theoretical value C, 81.60；H,4.23；N,14.17；
Test value: C, 81.55；H,4.20；N,14.25
HPLC-MS: material molecule amount 691.78 surveys molecular weight 691.84.
The synthesis of 12 compound 124 of embodiment
0.01mol intermediate G, 0.012mol intermediate h is added under the atmosphere for being passed through nitrogen in the four-hole bottle of 250ml,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-tert-butylphosphine, 150ml toluene is heated to reflux 24
Hour, contact plate, fully reacting are sampled, natural cooling filters, and filtrate revolving crosses silicagel column, obtains target product, purity
98.82%, yield 61.20%.
Elemental analysis structure (molecular formula C46H28N8): theoretical value C, 79.75；H,4.07；N,16.17；
Test value: C, 79.84；H,4.10；N,16.06
HPLC-MS: material molecule amount 692.77 surveys molecular weight 692.70.
The compounds of this invention can be used as emitting layer material use, to the compounds of this invention 14, compound 64 and existing material
Material CBP carries out the measurement of hot property, luminescent spectrum, T1 energy level and cyclic voltammetric stability, testing result such as 1 institute of table respectively
Show.
Table 1
| Compound | Td(℃) | λPL(nm) | Cyclic voltammetric stability | T1 energy level (eV) |
| Compound 14 | 390 | 370 | It is excellent | 3.0 |
| Compound 64 | 402 | 375 | It is excellent | 2.98 |
| Material C BP | 353 | 369 | Difference | 2.7 |
Note: thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, opens up Pu Kang using Japan
The measurement of SR-3 spectroradiometer；Cyclic voltammetric stability be by cyclic voltammetry observe material redox characteristic come into
Row identification；Test condition: test sample is dissolved in the methylene chloride and acetonitrile mixed solvent that volume ratio is 2:1, concentration 1mg/mL, electricity
Solving liquid is the tetrabutyl ammonium tetrafluoroborate of 0.1M or the organic solution of hexafluorophosphate.Reference electrode is Ag/Ag+ electricity
Pole is titanium plate to electrode, and working electrode is ITO electrode, and cycle-index is 20 times.T1 is the phosphorescent emissions light for first testing compound
Spectrum, and be calculated by phosphorescent emissions peak and (test equipment: utilize the FLS980 fluorescence spectrum of Edinburgh Instruments
Instrument, the Optistat DN-V2 cryogenic assembly of Oxford Instruments).
By upper table data it is found that the compounds of this invention have preferable oxidation-reduction stability, higher thermal stability, compared with
High T1 energy level, is suitable as the material of main part of luminescent layer；Meanwhile the compounds of this invention contain electron donor (donor, D) with
Electron acceptor (acceptor, A), so that the OLED device electrons and holes using the compounds of this invention reach equilibrium state, device
Part efficiency and service life get a promotion.
Compound 14, compound 64, compound 77, compound 106, CBP as material of main part respectively and guest materials
Bis- (4,6- difluorophenyl pyridinato-N, the C2) pyridinecarboxylics of FIrpic[close iridium] (triplet T1=2.65eV) steaming altogether, it is formed
The organic film that the quality doping concentration of guest materials FIrpic is 8%.Organic film is irradiated by the ultraviolet light of 365nm,
Survey the fluorescence quantum efficiency (PLQY) of its organic film；Simultaneously measure LT50 (light emission luminance decay to original intensity 50% when
Between).Test result is as shown in table 2:
Table 2
| Organic film (15nm) | PLQY | Main body T1 | Main body Tg | LT50 |
| Compound 14:FIrpic (8wt%) | 100% ± 3 | 2.98eV | 124℃ | 7.0h |
| Compound 64:FIrpic (8wt%) | 95% ± 2 | 2.88eV | 120℃ | 6.4h |
| Compound 77:FIrpic (8wt%) | 92% ± 3 | 2.85eV | 114℃ | 5.8h |
| Compound 106:FIrpic (8wt%) | 90% ± 2 | 2.80eV | 110℃ | 5.5h |
| CPB:FIrpic (8wt%) | 85 ± 3% | 2.70eV | 90℃ | 3.0h |
Note: organic film carries out double source by ANS evaporated device and steams altogether, and vapor deposition substrate is high saturating quartz glass, FIrpic's
Adulterating mass concentration is 10%.After vapor deposition, (concentration of water and oxygen be less than 1ppm) is packaged in glove box.Glass
Change transition temperature (Tg) using Japanese Shimadzu DSC-60 test macro；PLQY (absolute fluorescence quantum efficiency) is using Japan
HAMAMAT (C11347-11Quantaurus-QY) test macro；LT50 uses Shanghai University OLED life-span test system.
It can see by upper table data, relative to convention body material C PB, organic film made by the compound of the present invention
PLQY and LT50 with higher.The reason is that the T of the compounds of this invention1Energy level is high, energy can be effectively prevent to mix from object
Miscellaneous material returns material of main part；Meanwhile the compounds of this invention glass transition temperature with higher, it can effectively prevent organic
Film crystallization, effectively improves the service life of organic film.
Calculate by HOMO, lumo energy of the quantum-mechanical effects software ORCA to the compounds of this invention and go forward side by side
Row visualization, calculation method use B3LYP hydridization functional, base group 6-31g (d).The effect of visualization of compound 14 such as Fig. 2 institute
Show；The effect of visualization of compound 64 is as shown in Figure 3；The effect of visualization of compound 77 is as shown in Figure 4；Compound 106 can
It is as shown in Figure 5 depending on changing effect.
The 13-22 and comparative example 1-3 compound conduct in the devices that the present invention will be described in detail synthesizes by the following examples
The application effect of luminescent layer material of main part.Embodiment 14-22 is compared with embodiment 13, the complete phase of the manufacture craft of the device
Together, and identical baseplate material and electrode material are used, the film thickness of electrode material is also consistent, except that device
Emitting layer material is changed in part.Embodiment 13-22 is compared with comparative example 1-3, the luminescent layer material of device described in comparative example 1
Material is using existing common raw material, and the device emitting layer material of embodiment 13-22 is using the compounds of this invention.Each reality
The structure composition for applying an obtained device is as shown in table 3；The performance test results of each device are as shown in table 4.
Embodiment 13
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 3 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).The molecular structural formula of associated materials is such as
Shown in lower:
Specific preparation process is as follows:
Transparent substrate layer 1 uses transparent material.Ito anode layer 2 (film thickness 150nm) is washed, i.e., is successively carried out
Ultraviolet-ozone washing is carried out after neutralizing treatment, pure water, drying again to remove the organic residue on the transparent surface ITO.
On having carried out the ito anode layer 2 after above-mentioned washing, using vacuum deposition apparatus, it is 10nm's that film thickness, which is deposited,
Molybdenum trioxide MoO3It is used as hole injection layer 3.And then the TAPC of 80nm thickness is deposited as hole transmission layer 4.
After above-mentioned hole mobile material vapor deposition, the luminescent layer 5 of OLED luminescent device is made, structure includes OLED hair
The used material compound 1 of photosphere 5 is used as material of main part, and for GD-19 as dopant material, dopant material doping ratio is 5% weight
Ratio is measured, luminescent layer film thickness is 30nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are TPBI.The vacuum evaporation coating of the material
Thickness is 40nm, this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, lithium fluoride (LiF) layer that film thickness is 1nm is made, this layer is
Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, aluminium (Al) layer that film thickness is 80nm is made, this layer is cathode
Reflection electrode layer 8 uses.
After completing OLED luminescent device as described above, anode and cathode is connected with well known driving circuit, is surveyed
The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.
Embodiment 14
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 5 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 15
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 14 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 16
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 35 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 17
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 47 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 18
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 64 and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 19
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 70 and Ir (PPy) 3 according to 100:10, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 20
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 77 and Ir (PPy) 3 according to 100:10, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 21
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 91 and GD-PACTZ according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 22
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 106 and GD-PACTZ according to 100:5, thickness 30nm)/electron transfer layer 6
(TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 23
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 107, GH-204 and Ir (PPy) 3 according to 70:30:10, thickness 30nm)/electricity
Sub- 6 (TPBI, thickness 40nm)/electron injecting layer of transport layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Embodiment 24
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of compound 124, GH-204 and GD-PACTZ according to 70:30:5, thickness 30nm)/electricity
Sub- 6 (TPBI, thickness 40nm)/electron injecting layer of transport layer, 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 1
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of CBP and GD-19 according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI, thickness
40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 2
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of CBP and Ir (PPy) 3 according to 100:10, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/cathode reflection electrode layer 8 (Al).
Comparative example 3
2/ hole injection layer of ito anode layer, 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness
80nm)/luminescent layer 5 (the weight ratio blending of CBP and GD-PACTZ according to 100:5, thickness 30nm)/electron transfer layer 6 (TPBI,
Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode layer 8 (Al).
The test result of made OLED luminescent device is shown in Table 4.
Table 3
Table 4
| Device code name | Current efficiency | Color | The LT95 service life |
| Embodiment 13 | 12.0 | Green light | 15.2 |
| Embodiment 14 | 10.8 | Green light | 11.5 |
| Embodiment 15 | 10.3 | Green light | 11.0 |
| Embodiment 16 | 9.5 | Green light | 10.5 |
| Embodiment 17 | 9.7 | Green light | 8.20 |
| Embodiment 18 | 12.0 | Green light | 12.3 |
| Embodiment 19 | 26.0 | Green light | 14.0 |
| Embodiment 20 | 28.3 | Green light | 12.4 |
| Embodiment 21 | 28.0 | Green light | 12.8 |
| Embodiment 22 | 30.2 | Green light | 14.5 |
| Embodiment 23 | 34.8 | Green light | 21.5 |
| Embodiment 24 | 32.5 | Green light | 16.0 |
| Comparative example 1 | 6.5 | Green light | 3.8 |
| Comparative example 2 | 24.6 | Green light | 4.3 |
| Comparative example 3 | 25.1 | Green light | 7.8 |
Illustrate: for device detection performance using comparative example 1 as reference, 1 device performance indexes of comparative example is set as 1.0.Than
Current efficiency compared with example 1 is 6.5cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.32,0.61)；The LT95 service life under 5000 brightness
Decay to 3.8Hr.Life-span test system is owner of the present invention and the OLED device life test that Shanghai University is studied jointly
Instrument.
The result of table 4 can be seen that compound of the present invention can be applied and OLED photophore as luminescent layer material of main part
Part production, and compared with comparative example 1, either efficiency or service life obtain larger change than known OLED material, especially
It is the driving service life biggish promotion of acquisition of device.
From the point of view of above data application, the compounds of this invention has in OLED luminescent device good as emitting layer material
Application effect, have good industrialization prospect.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that it is public that the present invention is not limited to institutes
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
Attached the scope of the claims should be consistent with widest explanation to cover all such modifications and similar arrangement.
Claims (5)
1. a kind of using benzimidazole and ring is the compound of core skeleton, it is characterised in that the structure of the compound such as general formula
(1) shown in:
In general formula (1), X1、X2、X3、X4、Y1、Y2、Y3、Y4Independently be expressed as carbon atom or nitrogen-atoms；And X1、X2、X3、
X4At most there is one to be expressed as nitrogen-atoms；Y1、Y2、Y3、Y4At most there is one to be expressed as nitrogen-atoms；X1、X2、X3、X4、Y1、Y2、Y3、
Y4At least one is expressed as nitrogen-atoms；
Z1It is expressed as one of the tertiary amine groups that oxygen atom, sulphur atom, aryl replace；The aryl is substitution or unsubstituted
Any one of phenyl, pyrimidine radicals, xenyl, quinolyl；
N=0, m=1 or n=1, m=0.
2. compound according to claim 1, it is characterised in that the structure of the compound is by any in following general formula
Kind indicates:
Wherein, X1、X2、X3、X4、Y1、Y2、Y3、Y4Independently be expressed as carbon atom or nitrogen-atoms；And X1、X2、X3、X4Extremely
There is one to be expressed as nitrogen-atoms more；Y1、Y2、Y3、Y4At most there is one to be expressed as nitrogen-atoms；
R1It is expressed as any one of substitution or unsubstituted phenyl, pyrimidine radicals, xenyl, quinolyl.
3. compound according to claim 1, it is characterised in that the concrete structure formula of the compound are as follows:
Any one of.
4. a kind of luminescent device comprising any one of claims 1 to 3 compound, it is characterised in that the compound conduct
The material of main part of luminescent layer, for making organic electroluminescence device.
5. a kind of method for preparing any one of claims 1 to 3 compound, it is characterised in that is occurred in preparation process is anti-
Answer equation are as follows:
N=0, m=1 or n=1, m=0；
X is expressed as one of the tertiary amine groups that oxygen atom, sulphur atom, alkyl or aryl replace；
The preparation method is as follows:
Weigh bromo-derivative, the Ar of benzimidazole and ring1- H is dissolved with toluene；Add Pd2(dba)3, tri-tert-butylphosphine, the tert-butyl alcohol
Sodium；Under an inert atmosphere, it by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reacts 10~24 hours, it is cooling
And filtering reacting solution, filtrate revolving cross silicagel column, obtain target product；
The bromo-derivative and Ar of the benzimidazole and ring1- H molar ratio is 1:0.8~2.0:0.8~2.0, Pd2(dba)3With benzo
The molar ratio of the bromo-derivative of imidazo ring is 0.006~0.02:1, and tri-tert-butylphosphine rubs with the bromo-derivative of benzimidazole and ring
, than being 0.006~0.02:1, sodium tert-butoxide is 1.0~3.0:1 with the molar ratio of benzimidazole and the bromo-derivative of ring for you.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015014791A1 (en) * | 2013-07-30 | 2015-02-05 | Basf Se | Benzimidazolo[2,1-b][1,3]benzothiazoles for electronic applications |
| CN104662023A (en) * | 2012-09-20 | 2015-05-27 | 巴斯夫欧洲公司 | Azadibenzofurans for electronic applications |
| CN104693105A (en) * | 2013-12-05 | 2015-06-10 | 乐金显示有限公司 | Organic compound and organic light emitting diode using the same |
| WO2016016791A1 (en) * | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
| EP2982676A1 (en) * | 2014-08-07 | 2016-02-10 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
-
2016
- 2016-11-08 CN CN201610979675.4A patent/CN106543205B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104662023A (en) * | 2012-09-20 | 2015-05-27 | 巴斯夫欧洲公司 | Azadibenzofurans for electronic applications |
| WO2015014791A1 (en) * | 2013-07-30 | 2015-02-05 | Basf Se | Benzimidazolo[2,1-b][1,3]benzothiazoles for electronic applications |
| CN104693105A (en) * | 2013-12-05 | 2015-06-10 | 乐金显示有限公司 | Organic compound and organic light emitting diode using the same |
| WO2016016791A1 (en) * | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
| EP2982676A1 (en) * | 2014-08-07 | 2016-02-10 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
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