CN106467510A - A kind of electroluminescent organic material and its application - Google Patents

A kind of electroluminescent organic material and its application Download PDF

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CN106467510A
CN106467510A CN201610412487.3A CN201610412487A CN106467510A CN 106467510 A CN106467510 A CN 106467510A CN 201610412487 A CN201610412487 A CN 201610412487A CN 106467510 A CN106467510 A CN 106467510A
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formula
organic material
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electroluminescent organic
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李崇
叶中华
王立春
张兆超
徐凯
于凯朝
刘琼文
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Abstract

The invention discloses a kind of electroluminescent organic material and its application, shown in the structural formula such as formula (1) of this kind of material.This kind of material has good fluorescence quantum efficiency and electroluminescent efficiency, easily forms armorphous thin film, has good heat stability, therefore such material can use as luminescent layer material of main part or dopant material in organic electroluminescence device.

Description

A kind of electroluminescent organic material and its application
Technical field
The present invention relates to technical field of semiconductors, especially relate to a kind of fluorescent chemicalses, and as emitting layer material Application 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 be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is quite varied.
Currently, in smart mobile phone, the field such as panel computer obtains application to OLED Display Technique, further also will be to electricity Depending on etc. large scale application extension.But, require to compare with the products application of reality, the luminous efficiency of OLED, use The performances such as life-span also need to be lifted further.
OLED luminescent device just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute OLED luminescent device together. As current device, when the two end electrodes applied voltage to OLED luminescent device, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is compound in luminescent layer further, that is, produce OLED electroluminescent.
High performance research is carried for OLED luminescent device include：Reduce the driving voltage of device, improve the luminous of device Efficiency, improves service life of device etc..In order to realize the continuous lifting of the performance of OLED, not only need from OLED Structure and the innovation of processing technology, constantly study with greater need for oled light sulfate ferroelectric functional material and innovate, formulate out higher performance OLED Functional material.
The oled light sulfate ferroelectric functional material being applied to OLED can be divided into two big class from purposes, i.e. electric charge injection transmission Material and luminescent material, further, also can inject charge into transmission material and be divided into electron injection transmission material and hole injection to pass Luminescent material can also be divided into main body luminescent material and dopant material by defeated material.In order to make high performance OLED luminous organ Part it is desirable to various organic functional material possesses good photoelectric characteristic, such as, as charge transport materials it is desirable to have good Carrier mobility, high-vitrification conversion temperature etc., the material requirements material as luminescent layer has good fluorescent quantum Efficiency, material evaporation stability, suitable HOMO/LUMO energy rank etc..
The oled light sulfate ferroelectric functional material film layer constituting OLED at least includes the above structure of two-layer, application in industry OLED structure, then include multiple film layer such as hole injection layer, hole transmission layer, luminescent layer, electron injecting layer that is to say, that The photoelectric functional material being applied to OLED includes at least hole-injecting material, hole mobile material, luminescent material, and electronics is noted Enter material etc., material type and collocation form have rich and multifarious feature.In addition, the OLED device for different structure For part collocation, the photoelectric functional material being used has stronger selectivity, and identical material is in different structure device Performance is it is also possible to completely totally different.
At present, fluorescent material research aspect has been achieved for significant progress, disclosure satisfy that the demand of industrialization；But its Efficiency, life-span aspect still Shortcomings, are difficult to reach the requirement of full-color RGB.Thus, there is high efficiency, long-life fluorescence The research and development of material is always the focus of industrialization.
Therefore, for the actual demand that current OLED shows Lighting Industry, the development of fluorescent material is also far from enough, Lag behind the requirement of panel manufacturing enterprise, the exploitation as the organic functionses fluorescent material of material enterprise development higher performance seems Particularly important.
Content of the invention
The problems referred to above existing for prior art, the applicant provides a kind of electroluminescent organic material and its answers With.The OLED that the present invention produces has good external quantum efficiency, stability of material and excitation, disclosure satisfy that face The requirement of plate manufacturing enterprise.
Technical scheme is as follows：
A kind of electroluminescent organic material, shown in the structure such as formula (1) of described electroluminescent organic material：
In formula (1), R1、R2Separately represent triaromatic amine group or nitrogenous multicomponent heterocycle aromatic group； R1、R2Identical or different；
In formula (1), X is oxygen atom, sulphur atom, selenium atom, dimethyl-silicon, C1-10The Asia that straight or branched alkyl replaces One of amido that alkyl, the alkylidene of aryl replacement, alkyl or aryl replace.
R in described formula (1)1、R2All can be represented using formula (2)：
Wherein, R3、R4Separately be expressed as substituted or unsubstituted phenyl, pyridine radicals, dibiphenylyl, terphenyl, Anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, click One of oxazolyl, benzo carbazole base, dibenzothiophenes base, bifurcation piperidinyl, indolocarbazole base, phenazinyl, thiazinyl； R3、R4Identical or different.
R in described formula (2)3、R4It is separately：
In any one.
Preferably, in described formula (1), R1、R2All can be represented using formula (3)：
In formula (3), X1For oxygen atom, sulphur atom, selenium atom, dimethyl-silicon, C1-10The Asia that straight or branched alkyl replaces One of amido that alkyl, the alkylidene of aryl replacement, alkyl or aryl replace.
Preferably, in described formula (1), R1、R2Using any one expression in formula (4) or formula (5)：
Wherein, R5、R6Selection hydrogen independently or structure shown in formula (6)：
A isX2、X3It is respectively oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkane One of amido that the alkylidene of base replacement, the alkylidene of aryl replacement, alkyl or aryl replace；A 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’5Bonded.
Preferably, the concrete structure of described compound is：
In any one.
A kind of organic electroluminescence device containing described electroluminescent organic material, described electroluminescent organic material is made It is luminescent layer material of main part or dopant material is applied to organic electroluminescent LED.
Beneficial the having technical effect that of the present invention：
OLED material of the present invention can be applicable to OLED luminescent device and makes, and can obtain good device table Existing, when described material uses as the luminescent layer material of main part of OLED luminescent device or dopant material, the luminous efficiency of device, Power efficiency and external quantum efficiency are all greatly improved；Device color color purity be improved significantly, device lifetime gets a promotion.This Invent described OLED material and there is in OLED luminescent device good application effect, there is good industrialization prospect.
With framing structure shown in formula (1), as core, this core has good the electroluminescent organic material of the present invention Fluorescence quantum efficiency, is modified by different substituent groups on core skeleton, effectively improve the heat stability of material with Excitation.Efficiency and the life-span of OLED by such material application in organic OLED devices, can be effectively improved.
Brief description
The schematic diagram of the OLED that Fig. 1 makes for the compounds of this invention.
In figure：1st, it is transparent substrate layer, 2, be ito anode layer, 3, be hole injection layer, 4, be hole transmission layer, 5, be Luminescent layer, 6, be electron transfer layer, 7, be electron injecting layer, 8, be negative electrode reflection electrode layer.
Fig. 2 is the structural formula of critical materialses used by device in the embodiment of the present invention 17.
Specific embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
Embodiment 1 (compound 01)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 5.16 grams of (0.01M) intermediate A, 4.23 grams of (0.025M) hexichol Amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA【Normal-butyl two (1- adamantyl) phosphine】, 200ml Toluene, is heated to reflux 18 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol= 2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 5.15 grams of white solids after recrystallization, and purity (HPLC) is 98.4%, yield 74.4%.
Elementary analysiss structure (molecular formula C51H36N2O)：Theoretical value C, 88.41；H,5.24；N,4.04；O, 2.31；
Test value：C,88.24；H,5.05；N,3.88；O,2.83.
Embodiment 2 (compound 03)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, 5.16 grams of (0.01M) intermediate A, 6.33 grams (0.025M) double (3- isopropyl Base phenyl) amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) Phosphine), 200ml toluene, it is heated to reflux 26 hours, reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene: Ethanol=2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 6.76 grams of white solids, purity (HPLC) is after recrystallization 98.62%, yield 78.5%.
Elementary analysiss structure (molecular formula C63H60N2O)：Theoretical value C, 87.87；H,7.02；N,3.25；O,1.86；
Test value：C,88.01；H,6.86；N,3.05；O,2.08.
Embodiment 3 (compound 04)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds in the middle of 5.16 grams of (0.01M) intermediate A, 7.53 grams (0.025M) Body a, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml toluene, is heated to reflux 24 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol =2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 6.02 grams of white solids after recrystallization, and purity (HPLC) is 99.01%, receives Rate 62.9%.
Elementary analysiss structure (molecular formula C69H52N2O3)：Theoretical value C, 86.58；H,5.48；N,2.93；O,5.01；
Test value：C,86.29；H,5.67；N,2.88；O,5.16.
Embodiment 4 (compound 55)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 5.16 grams of (0.01M) intermediate B, 4.23 grams of (0.025M) hexichol Amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml Toluene, is heated to reflux 28 hours, and reaction is completely.Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol= 2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 5.19 grams of white solids after recrystallization, and purity (HPLC) is 98.64%, yield 74.9%.
Elementary analysiss structure (molecular formula C51H36N2O)：Theoretical value C, 88.41；H,5.24；N,4.04；O,2.31；
Test value：C,88.25；H,5.15；N,4.15；O,2.45.
Embodiment 5 (compound 56)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 5.16 grams of (0.01M) intermediate C, 4.23 grams of (0.025M) hexichol Amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml Toluene, is heated to reflux 22 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol= 2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 5.0 grams of white solids after recrystallization, and purity (HPLC) is 98.24%, yield 72.2%.
Elementary analysiss structure (molecular formula C51H36N2O)：Theoretical value C, 88.41；H,5.24；N,4.04；O,2.31；
Test value：C,88.35；H,5.13；N,4.09；O,2.43.
Embodiment 6 (compound 09)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, nitrogen protection under, add 5.32 grams of (0.01M) intermediate E, 4.62 grams (0.025M) double (3, 4- 3,5-dimethylphenyl) amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- Buddha's warrior attendant Alkyl) phosphine), 200ml toluene, it is heated to reflux 25 hours, reaction is completely.Natural cooling, filters, filtrate revolving, crosses silicagel column, uses Toluene:Ethanol=2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 6.44 grams of white solids, purity (HPLC) is after recrystallization 97.86%, yield 78.5%.
Elementary analysiss structure (molecular formula C59H52N2S)：Theoretical value C, 86.30；H,6.38；N,3.41；O,3.91；
Test value：C,86.25；H,6.50；N,3.51；O,3.74.
Embodiment 7 (compound 11)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds in the middle of 5.32 grams of (0.01M) intermediate E, 7.53 grams (0.025M) Body a, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml toluene, is heated to reflux 23 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol =2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 6.66 grams of white solids after recrystallization, and purity (HPLC) is 98.75%, receives Rate 68.4%.
Elementary analysiss structure (molecular formula C69H52N2O2S)：Theoretical value C, 85.15；H,5.39；N,2.88；O,3.29；S, 3.29；
Test value：C,85.04；H,5.47；N,2.78；O,3.45；S,3.26.
Embodiment 8 (compound 12)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds in the middle of 5.32 grams of (0.01M) intermediate E, 8.18 grams (0.025M) Body c, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml toluene, is heated to reflux 22 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol =2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 7.05 grams of white solids after recrystallization, and purity (HPLC) is 98.60%, receives Rate 68.8%.
Elementary analysiss structure (molecular formula C75H64N2S)：Theoretical value C, 87.85；H,6.29；N,2.73；S,3.13；
Test value：C,88.05；H,6.18；N,2.84；S,2.93.
Embodiment 9 (compound 58)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 5.32 grams of (0.01M) intermediate F, 4.23 grams of (0.025M) hexichol Amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml Toluene, is heated to reflux 20 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol= 2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 5.49 grams of white solids after recrystallization, and purity (HPLC) is 98.36%, yield 77.4%.
Elementary analysiss structure (molecular formula C51H36N2S)：Theoretical value C, 86.41；H,5.12；N,3.95；S,4.52；
Test value：C,86.52；H,5.01；N,3.78；S,4.69.
Embodiment 10 (compound 13)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 5.91 grams of (0.01M) intermediate G, 4.23 grams of (0.025M) hexichol Amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml Toluene, is heated to reflux 26 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol= 2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 5.80 grams of white solids after recrystallization, and purity (HPLC) is 98.46%, yield 75.5%.
Elementary analysiss structure (molecular formula C57H41N3)：Theoretical value C, 89.15；H,5.38；N,5.47；
Test value：C,88.97；H,5.42；N,5.61.
Embodiment 11 (compound 19)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 5.42 grams of (0.01M) intermediate H, 4.23 grams of (0.025M) hexichol Amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml Toluene, is heated to reflux 22 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol= 2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 5.21 grams of white solids after recrystallization, and purity (HPLC) is 98.04%, yield 72.5%.
Elementary analysiss structure (molecular formula C54H42N2)：Theoretical value C, 90.21；H,5.89；N,3.90；
Test value：C,90.05；H,5.78；N,4.17.
Embodiment 12 (compound 25)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 5.58 grams of (0.01M) intermediate compound I, 4.23 grams of (0.025M) hexichol Amine, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml Toluene, is heated to reflux 24 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol= 2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 5.20 grams of white solids after recrystallization, and purity (HPLC) is 98.50%, yield 70.8%.
Elementary analysiss structure (molecular formula C53H42N2Si1)：Theoretical value C, 86.61；H,5.76；N,3.81；Si, 3.82；
Test value：C,86.52；H,5.88；N,3.90；Si,3.70.
Embodiment 13 (compound 37)
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under nitrogen protection, adds in the middle of 5.16 grams of (0.01M) intermediate A, 5.23 grams (0.025M) Body b, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml toluene, is heated to reflux 28 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol =2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains gram 5.76 grams of white solids after recrystallization, and purity (HPLC) is 98.66%, Yield 74.5%.
Elementary analysiss structure (molecular formula C57H44N2O)：Theoretical value C, 88.57；H,5.74；N,3.62；O,2.07；
Test value：C,88.42；H,5.86；N,3.57；O,2.15.
Embodiment 14 (compound 43)
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under nitrogen protection, adds in the middle of 5.42 grams of (0.01M) intermediate H, 5.23 grams (0.025M) Body b, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml toluene, is heated to reflux 25 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol =2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains gram 6.07 grams of white solids after recrystallization, and purity (HPLC) is 98.46%, Yield 76.0%.
Elementary analysiss structure (molecular formula C60H50N2)：Theoretical value C, 90.19；H,6.31；N,3.51；
Test value：C,90.05；H,6.40；N,3.55.
Embodiment 15 (compound 50)
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under nitrogen protection, adds in the middle of 5.16 grams of (0.01M) intermediate A, 7.48 grams (0.025M) Body d, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml toluene, is heated to reflux 30 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol =2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 6.62 grams of white solids after recrystallization, and purity (HPLC) is 98.01%, receives Rate 69.5%.
Elementary analysiss structure (molecular formula C69H48N2O3)：Theoretical value C, 86.95；H,5.08；N,2.94；O,5.04；
Test value：C,87.05；H,5.14；N,2.87；O,4.94.
Embodiment 16 (compound 60)
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under nitrogen protection, adds in the middle of 5.42 grams of (0.01M) intermediate H, 6.83 grams (0.025M) Body e, 1.15 grams of (0.012M) sodium tert-butoxides, 0.1 gram of palladium, 0.05 gram of CXA (normal-butyl two (1- adamantyl) phosphine), 200ml toluene, is heated to reflux 30 hours, and reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol =2.5:1 (volume ratio) mixed solvent is pulled an oar, and obtains 6.50 grams of white solids after recrystallization, and purity (HPLC) is 98.24%, receives Rate 70.15%.
Elementary analysiss structure (molecular formula C66H42N2O4)：Theoretical value C, 85.51；H,4.57；N,3.02；O,6.90；
Test value：C,85.47；H,4.62；N,2.95；O,6.96.
By the following examples 17 and comparative example 1～16 describe in detail the present invention synthesis material in OLED should Use effect., compared with embodiment 17, the processing technology of described device is identical, and is employed for described comparative example 1～16 Identical baseplate material and electrode material, the thickness of electrode material is also consistent, except that to used in device Portion of material has carried out some adjustment, and comparative example employs part OLED material of the present invention.Device architecture is as shown in table 1.
Embodiment 17
As shown in figure 1, transparent substrate layer 1 adopts transparent material, such as glass.Ito anode layer 2 (thickness is 150nm) is entered Row washing, carry out successively neutralizing treatment, pure water, be dried after carry out again ultraviolet-ozone wash to remove transparent ITO surface Organic residue.
On the ito anode layer 2 having carried out after above-mentioned washing, using vacuum deposition apparatus, it is deposited with HAT-CN, its thickness For 10nm, this layer of organic material uses as hole injection layer 3.And then evaporation 60nm thickness TCTA (4,4', 4 "-three (clicks Azoles -9- base) triphenylamine) as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, make the luminescent layer 5 of OLED luminescent device, its structure includes OLED and sends out Used material C BP of photosphere 5【4,4'- bis- (9- carbazole) biphenyl】As material of main part, MQAB is as dopant material, doping ratio For 5% weight ratio, luminescent layer thickness is 25nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are Alq3(8-hydroxyquinoline aluminum).This material The vacuum evaporation thickness of material is 30nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, make lithium fluoride (LiF) layer that thickness is 1nm, this layer is Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminum (Al) layer that thickness is 80nm, this layer is negative electrode Reflection electrode layer 8 uses.Layers of material structure is as shown in Figure 2.
After OLED luminescent device accomplished as described above, with known drive circuit, anode and negative electrode are coupled together, survey The luminous efficiency of metering device, glow color, external quantum efficiency and device lifetime (LT90：Original intensity is arrived in brightness decay 90%).Its result is shown in table 2：
Comparative example 1
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 1 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 2
This comparative example is with part with embodiment 17：MQAB in the luminescent layer 5 of OLED luminescent device changes into enforcement The test result of the OLED luminescent device made by the material that example 2 prepares is as shown in table 1.
Comparative example 3
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 3 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 4
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 4 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 5
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 5 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 6
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 6 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 7
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 7 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 8
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 8 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 9
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 9 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 10
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 10 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 11
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 11 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 12
This comparative example is with embodiment 17 difference：MQAB in the luminescent layer 5 of OLED luminescent device changes into reality Apply the material that example 12 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 13
This comparative example is with embodiment 17 difference：CPB in the luminescent layer 5 of OLED luminescent device changes into enforcement The material that example 13 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 14
This comparative example is with embodiment 17 difference：CPB in the luminescent layer 5 of OLED luminescent device changes into enforcement The material that example 14 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 15
This comparative example is with embodiment 17 difference：CPB in the luminescent layer 5 of OLED luminescent device changes into enforcement The material that example 15 prepares.The test result of made OLED luminescent device is as shown in table 1.
Comparative example 16
This comparative example is with embodiment 17 difference：CPB in the luminescent layer 5 of OLED luminescent device changes into enforcement The material that example 16 prepares.The test result of made OLED luminescent device is as shown in table 1.
Table 1
Table 2
Note：Data above is all using embodiment 17 as normal component, and embodiment 17 obtained device in luminosity is 1000cd/m2When, luminous efficiency is 3.6cd/A, and external quantum efficiency is 3.0%；(luminosity is original intensity to drive the life-span 90%) be 30 hours
OLED material of the present invention be can be seen that by the result of table 2 and can be applicable to the making of OLED luminescent device, and can To obtain good device performance.The luminous efficiency of device, external quantum efficiency are all greatly improved；Device lifetime lifting simultaneously Clearly.OLED material of the present invention has good application effect in OLED luminescent device, and has good product Industry prospect.
Although the present invention has been disclosed by embodiment and preferred implementation it should be appreciated that the invention is not restricted to institute's public affairs The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute The scope of attached claim should arrangement to cover all such modifications and be similar to consistent with explanation the widest.

Claims (7)

1. a kind of electroluminescent organic material is it is characterised in that the structure such as formula (1) of described electroluminescent organic material is shown：
In formula (1), R1、R2Separately represent triaromatic amine group or nitrogenous multicomponent heterocycle aromatic group；R1、R2Phase Same or different；
In formula (1), X is oxygen atom, sulphur atom, selenium atom, dimethyl-silicon, C1-10The alkylidene of straight or branched alkyl replacement, One of amido that the alkylidene of aryl replacement, alkyl or aryl replace.
2. electroluminescent organic material according to claim 1 is it is characterised in that R in described formula (1)1、R2All using logical Formula (2) represents：
Wherein, R3、R4Separately it is expressed as substituted or unsubstituted phenyl, pyridine radicals, dibiphenylyl, terphenyl, anthracene Base, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, carbazole One of base, benzo carbazole base, dibenzothiophenes base, bifurcation piperidinyl, indolocarbazole base, phenazinyl, thiazinyl；R3、R4 Identical or different.
3. electroluminescent organic material according to claim 2 is it is characterised in that R in described formula (2)3、R4Independently Ground is：
In any one.
4. electroluminescent organic material according to claim 1 is it is characterised in that in described formula (1), R1、R2All adopt Formula (3) represents：
In formula (3), X1For oxygen atom, sulphur atom, selenium atom, dimethyl-silicon, C1-10The alkylene that straight or branched alkyl replaces One of amido that base, the alkylidene of aryl replacement, alkyl or aryl replace.
5. electroluminescent organic material according to claim 1 is it is characterised in that in described formula (1), R1、R2Using logical Any one expression in formula (4) or formula (5)：
Wherein, R5、R6Selection hydrogen independently or structure shown in formula (6)：
A isX2、X3It is respectively oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkyl takes One of amido that the alkylidene in generation, the alkylidene of aryl replacement, alkyl or aryl replace；A 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’5Bonded.
6. electroluminescent organic material according to claim 1 is it is characterised in that the concrete structure of described compound is：
In any one.
7. the organic electroluminescence device of electroluminescent organic material described in a kind of any one containing claim 1～6, its feature It is that described electroluminescent organic material is applied to organic electroluminescent two pole as luminescent layer material of main part or dopant material Pipe.
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CN110655486A (en) * 2018-06-29 2020-01-07 江苏三月光电科技有限公司 Compound with dibenzosuberene as core and application thereof
CN112321629A (en) * 2019-12-20 2021-02-05 广东聚华印刷显示技术有限公司 Spiro dibenzosuberene acridine compound and application thereof

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