CN106543205A - 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 PDF

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CN106543205A
CN106543205A CN201610979675.4A CN201610979675A CN106543205A CN 106543205 A CN106543205 A CN 106543205A CN 201610979675 A CN201610979675 A CN 201610979675A CN 106543205 A CN106543205 A CN 106543205A
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compound
layer
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nitrogen
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CN106543205B (en
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叶中华
李崇
徐凯
张小庆
张兆超
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract

The invention discloses a kind of compound with benzimidazole skeleton as core and its application on organic electroluminescence device, the compound is with benzimidazole and ring is as core, the class formation is difficult crystallization, and the characteristics of there is good filming, while with higher triplet and heat endurance.When the compounds of this invention is used as the luminescent layer material of main part of OLED luminescent devices, the current efficiency of device, power efficiency and external quantum efficiency are greatly improved；Lifted clearly simultaneously for device lifetime.

Description

A kind of compound containing benzimidazole and its application on OLED
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of compound containing benzimidazole, and its work The application for being emitting layer material on Organic Light Emitting Diode.
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 for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is quite varied.
OLED luminescent devices are 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 together OLED luminescent devices. As current device, when the two end electrodes applied voltage to OLED luminescent devices, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge are further combined in luminescent layer, that is, produce OLED electroluminescent.
In order to obtain the organic electroluminescence device of excellent combination property, need to design suitable Subjective and Objective material and optimization Device architecture, luminescent layer material of main part generally comprise hole and/or electric transmission unit, with suitable carrier transport Can, and require that its triplet energy level, higher than illuminator, so just can guarantee that triplet exciton is confined to luminescent layer.Additionally, being Realize carrier efficiently injection to drop low start voltage, material of main part should also be with relative to the suitable of neighbouring organic layer Energy level.
In recent years, bipolar host material is led in electroluminescent device because of the hole with balance and electronic carrier stream Domain attract attention, and the production that progressively moving towards the industrialization.
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, it is particularly important as the organic functional material of material enterprise development higher performance.
The content of the invention
For prior art exist the problems referred to above, the applicant provide a kind of compound containing benzimidazole and its Application on organic electroluminescence device.The compounds of this invention is with benzimidazole and ring is as core, used 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, disclosure satisfy that panel manufacture enterprise The requirement of industry.
Technical scheme is as follows：
The applicant provides a kind of with benzimidazole compound of the ring as core skeleton, and the structure of the compound is such as Shown in formula (1)：
In 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；
Z1The one kind being expressed as in 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 equal to 1 when different.
Preferably, the structure of the compound is represented by any one in below 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；
R1Be expressed as replace or unsubstituted phenyl, pyrimidine radicals, xenyl, quinolyl in any one.
It is furthermore preferred that the concrete structure formula of the compound is：
In any one.
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 For：
N=0 or 1；M=0 or 1；And m, n are equal to 1 when different；
X is expressed as the one kind in the tertiary amine groups that oxygen atom, sulphur atom, alkyl or aryl replace；
Preparation method is as follows：
Weigh bromo-derivative, the Ar of benzimidazole ring1- H toluene dissolves；Add Pd2(dba)3, tri-butyl phosphine, uncle Sodium butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95～110 DEG C of reaction temperature, react 10～24 hours, Cooling filtering reacting solution, filtrate revolving, cross silicagel column, obtain target product；
The bromo-derivative and Ar of the benzimidazole ring1- H mol ratios are 1:0.8～2.0:0.8～2.0, Pd2(dba)3With The mol ratio of the bromo-derivative of benzimidazole ring is 0.006～0.02:1, the bromo-derivative of tri-butyl phosphine and benzimidazole ring Mol ratio be 0.006～0.02:1, the mol ratio of sodium tert-butoxide and benzimidazole the bromo-derivative of ring is 1.0～3.0:1.
The present invention is beneficial to be had technical effect that：
The compounds of this invention is with benzimidazole and ring is as parent nucleus, reconnects aromatic heterocycle group, destroys molecular symmetry, So as to the crystallinity of saboteur, it is to avoid intermolecular aggtegation, the compound structure intramolecular includes electron donor The combination of (donor, D) and electron acceptor (acceptor, A) can improve mobility, the drop low start voltage in electronics and hole, Simultaneously ring has higher triplet energy level to parent nucleus benzimidazole, compound triplet exciton is confined in luminescent layer, improves and send out 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 applied to the making of OLED luminescent devices as emitting layer material, used as luminous layer main body Material can obtain good device performance, and the current efficiency of device, power efficiency and external quantum efficiency are greatly improved； Lifted clearly simultaneously for device lifetime.
Compound-material of the present invention has good application effect in OLED luminescent devices, with good industry Change prospect.
Description of the drawings
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.
Fig. 2～5 are respectively compound 14, compound 64, compound 77, the effect of visualization figure of 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 As, 0.012mol intermediate a, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.90, yield 54.68%.
Elementary 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 is 632.73, surveys molecular weight 632.59.
The synthesis of 2 compound 5 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol intermediate a, 0.012mol intermediate b, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 97.98%, yield 61.20%.
Elementary 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 is 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 Bs, 0.012mol, intermediate b, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 99.0%, yield 63.4%.
Elementary 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 is 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 Bs, 0.012mol, intermediate c, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.7%, yield 58.7%.
Elementary 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 is 632.73, surveys molecular weight 632.65.
The synthesis of 5 compound 47 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol intermediate C, 0.012mol intermediate e, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-butyl phosphines, 150ml toluene are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.60%, yield 61.30%.
Elementary 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 is 616.67, surveys molecular weight 616.61.
The synthesis of 6 compound 64 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol intermediate C, 0.012mol, intermediate a, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.3%, yield 59.2%.
Elementary 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 is 616.67, surveys molecular weight 616.59.
The synthesis of 7 compound 70 of embodiment
The four-hole bottle of 500ml, under the atmosphere for being passed through nitrogen, adds 0.01mol intermediate C, 0.015mol intermediate d, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 99.1%, yield 56.7%.
Elementary 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 is 616.67, surveys molecular weight 616.57.
The synthesis of 8 compound 77 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol intermediate D, 0.012mol intermediate f, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-butyl phosphines, 150ml toluene are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.80%, yield 58.80%.
Elementary 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 is 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 Es, 0.012mol intermediate g, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-butyl phosphines, 150ml toluene are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.50%, yield 59.50%.
Elementary 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 is 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 Es, 0.012mol intermediate f, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-butyl phosphines, 150ml toluene are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.65%, yield 58.20%.
Elementary 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 is 691.78, surveys molecular weight 691.70.
The synthesis of 11 compound 107 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol intermediate F, 0.012mol intermediate h, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-butyl phosphines, 150ml toluene are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 99.10%, yield 59.8%.
Elementary 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 is 691.78, surveys molecular weight 691.84.
The synthesis of 12 compound 124 of embodiment
The four-hole bottle of 250ml, under the atmosphere for being passed through nitrogen, adds 0.01mol intermediate G, 0.012mol intermediate h, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4mol tri-butyl phosphines, 150ml toluene are heated to reflux 24 Hour, sample point plate, reaction are complete, natural cooling, filter, filtrate revolving, cross silicagel column, obtain target product, purity 98.82%, yield 61.20%.
Elementary 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 is 692.77, surveys molecular weight 692.70.
The compounds of this invention can be used as emitting layer material, to the compounds of this invention 14, compound 64 and existing material Material CBP carries out the measure of hot property, luminescent spectrum, T1 energy levels 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 levels (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 in nitrogen atmosphere weightless 1% temperature, hot in the TGA-50H of Japanese Shimadzu Corporation It is measured on weight analysis instrument, nitrogen flow is 20mL/min；λPLBe sample solution fluorescence emission wavelengths, Pu Kang is opened up using Japan SR-3 spectroradiometers are determined；Cyclic voltammetric stability is to observe the redox characteristic of material entering by cyclic voltammetry Row identification；Test condition：Test sample is dissolved in volume ratio for 2:1 dichloromethane and acetonitrile mixed solvent, concentration 1mg/mL, electricity Solution liquid is the organic solution of the tetrabutyl ammonium tetrafluoroborate or hexafluorophosphate of 0.1M.Reference electrode is Ag/Ag+ electric Pole, is titanium plate to electrode, and working electrode is ITO electrode, and cycle-index is 20 times.T1 is the phosphorescent emissions light of first test compound Spectrum, and (test equipment is calculated by phosphorescent emissions peak：Using the FLS980 fluorescence spectrums of Edinburgh Instruments Instrument, the Optistat DN-V2 cryogenic assemblies of Oxford Instruments).
From upper table data, the compounds of this invention has a preferable oxidation-reduction stability, higher heat endurance, compared with High T1 energy levels, are 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 reach poised state, device using the OLED electronics and hole of the compounds of this invention Part efficiency and life-span get a promotion.
Compound 14, compound 64, compound 77, compound 106, CBP as material of main part respectively and guest materials FIrpic【Double (4,6- difluorophenyl pyridinato-N, C2) pyridinecarboxylics close iridium】(triplet T1=2.65eV) steams altogether, is formed The quality doping content of guest materials FIrpic is 8% organic film.Organic film is irradiated by the ultraviolet light of 365nm, Survey the fluorescence quantum efficiency (PLQY) of its organic film；Simultaneously measure LT50 (luminosity 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 devices and steams altogether, and evaporation substrate is high quartz glass thoroughly, FIrpic's Doping mass concentration is 10%.After evaporation is finished, (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 system；PLQY (absolute fluorescence quantum efficiency) is using Japan HAMAMAT (C11347-11Quantaurus-QY) test system；LT50 adopts Shanghai University's OLED life-span test systems.
Can be seen by upper table data, relative to convention body material C PB, the organic film made by the compound of the present invention With higher PLQY and LT50.Reason is the T of the compounds of this invention1Energy level is high, can effectively prevent energy from mixing from object Miscellaneous material returns material of main part；Meanwhile, the compounds of this invention has higher glass transition temperature, can effectively prevent organic Thin film crystallization, effectively improves the life-span of organic film.
The HOMO of the compounds of this invention, lumo energy are carried out by calculating and gone forward side by side by quantum-mechanical effects software ORCA Row visualization, computational methods adopt B3LYP hydridization functionals, base group 6-31g (d).The effect of visualization of compound 14 such as Fig. 2 institutes 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.
13-22 and comparative example 1-3 describes the compound conduct in the devices of present invention synthesis in detail by the following examples The application effect of luminescent layer material of main part.Embodiment 14-22 compared with embodiment 13, the complete phase of manufacture craft of the device Together, and employed identical baseplate material and electrode material, the thickness of electrode material is also consistent, except that device In part, emitting layer material there occurs change.Embodiment 13-22 compared with comparative example 1-3, the luminescent layer material of device described in comparative example 1 Material uses existing conventional raw material, and the device emitting layer material of embodiment 13-22 uses 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 (compound 3 and GD-19 are according to 100 for 80nm)/luminescent layer 5：5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode reflection electrode layer 8 (Al).The molecular structural formula of associated materials is such as Shown in lower：
Concrete preparation process is as follows：
Transparent substrate layer 1 adopts transparent material.Ito anode layer 2 (thickness is 150nm) is washed, i.e., is carried out successively Neutralizing treatment, pure water, ultraviolet-ozone washing is carried out again to remove the organic residue on transparent ITO surfaces after drying.
On ito anode layer 2 after above-mentioned washing has been carried out, using vacuum deposition apparatus, thickness is deposited with for 10nm's Molybdenum trioxide MoO3Use as hole injection layer 3.And then the TAPC of 80nm thickness is deposited with as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, the luminescent layer 5 of OLED luminescent devices is made, its structure includes that OLED sends out Used as material of main part, used as dopant material, dopant material doping ratio is 5% weight to GD-19 to 5 used material compound 1 of photosphere Amount ratio, luminescent layer thickness is 30nm.
After above-mentioned luminescent layer 5, it is TPBI to continue vacuum evaporation electron transport layer materials.The vacuum evaporation coating of the material Thick is 40nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, lithium fluoride (LiF) layer of the thickness for 1nm is made, this layer is Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, aluminium (Al) layer of the thickness for 80nm is made, this layer is negative electrode Reflection electrode layer 8 is used.
After OLED luminescent devices accomplished as described above, anode and negative electrode are coupled together with known drive circuit, 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 (compound 5 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 14 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 35 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 47 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 64 and GD-19 are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 70 and Ir (PPy) 3 are according to 100 for 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 77 and Ir (PPy) 3 are according to 100 for 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 91 and GD-PACTZ are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 106 and GD-PACTZ are according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 107, GH-204 and Ir (PPy) 3 are according to 70 for 80nm)/luminescent layer 5:30:10 weight is than blending, thickness 30nm)/electricity Sub- transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (compound 124, GH-204 and GD-PACTZ are according to 70 for 80nm)/luminescent layer 5:30:5 weight is than blending, thickness 30nm)/electricity Sub- transport layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (CBP and GD-19 is according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (CBP and Ir (PPy) 3 is according to 100 for 80nm)/luminescent layer 5:10 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/negative electrode 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 (CBP and GD-PACTZ is according to 100 for 80nm)/luminescent layer 5:5 weight is than blending, 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 devices is shown in Table 4.
Table 3
Table 4
Device code name Current efficiency Color The LT95 life-spans
Embodiment 13 12.0 Green glow 15.2
Embodiment 14 10.8 Green glow 11.5
Embodiment 15 10.3 Green glow 11.0
Embodiment 16 9.5 Green glow 10.5
Embodiment 17 9.7 Green glow 8.20
Embodiment 18 12.0 Green glow 12.3
Embodiment 19 26.0 Green glow 14.0
Embodiment 20 28.3 Green glow 12.4
Embodiment 21 28.0 Green glow 12.8
Embodiment 22 30.2 Green glow 14.5
Embodiment 23 34.8 Green glow 21.5
Embodiment 24 32.5 Green glow 16.0
Comparative example 1 6.5 Green glow 3.8
Comparative example 2 24.6 Green glow 4.3
Comparative example 3 25.1 Green glow 7.8
Explanation:Using comparative example 1 as reference, 1 device property indices of comparative example are set to 1.0 to device detection performance.Than Compared with example 1 current efficiency be 6.5cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.32,0.61)；The LT95 life-spans 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 result of table 4 can be seen that compound of the present invention as luminescent layer material of main part can using with OLED photophores Part makes, and compared with comparative example 1, either efficiency or life-span be than the larger change of known OLED material acquisition, especially It is the lifting for driving life-span acquisition larger of device.
From the point of view of data above application, the compounds of this invention has good in OLED luminescent devices as emitting layer material Application effect, with good industrialization prospect.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that the invention is not restricted to institute public The embodiment opened.Conversely, it will be understood by those skilled in the art which is intended to various modifications with similar arrangement.Therefore, institute The scope of attached claim should the arrangement to cover all such modifications and be similar to consistent with most wide explanation.

Claims (5)

1. it is a kind of with benzimidazole compound of the ring as core skeleton, it is characterised in that the structure of the compound such as formula (1) shown in：
In 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；
Z1The one kind being expressed as in 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 equal to 1 when different.
2. compound according to claim 1, it is characterised in that the structure of the compound by below formula in it is arbitrary Plant and represent：
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；
R1Be expressed as replace or unsubstituted phenyl, pyrimidine radicals, xenyl, quinolyl in any one.
3. compound according to claim 1, it is characterised in that the concrete structure formula of the compound is：
In any one.
4. a kind of luminescent device comprising compound described in any one of claims 1 to 3, 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 compound described in any one of claims 1 to 3, it is characterised in that what is occurred in preparation process is anti- The equation is answered to be：
N=0 or 1；M=0 or 1；And m, n are equal to 1 when different；
X is expressed as the one kind in the tertiary amine groups that oxygen atom, sulphur atom, alkyl or aryl replace；
Preparation method is as follows：
Weigh bromo-derivative, the Ar of benzimidazole ring1- H toluene dissolves；Add Pd2(dba)3, tri-butyl phosphine, the tert-butyl alcohol Sodium；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95～110 DEG C of reaction temperature, react 10～24 hours, cooling And filtering reacting solution, filtrate revolving, silicagel column is crossed, target product is obtained；
The bromo-derivative and Ar of the benzimidazole ring1- H mol ratios are 1:0.8～2.0:0.8～2.0, Pd2(dba)3With benzo The mol ratio of the bromo-derivative of imidazo ring is 0.006～0.02:1, tri-butyl phosphine and benzimidazole the bromo-derivative of ring rub You are than being 0.006～0.02:1, the mol ratio of sodium tert-butoxide and benzimidazole the bromo-derivative of ring is 1.0～3.0:1.
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