CN105646500A - Diimidazo-pyrazine derivative and application thereof - Google Patents
Diimidazo-pyrazine derivative and application thereof Download PDFInfo
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Abstract
The invention provides a diimidazo-pyrazine derivative and application thereof. The novel compound is stable in property and simple in preparation technology, has high glass-transition temperature and high carrier mobility and can be used as an electron transmission layer of an OLED device, driving voltage can be obviously reduced in the device where the compound is applied, and the current efficiency is improved. Please see the general formula of the structure of the compound in the description, wherein Ar is aromatic groups, and R is one of hydrogen, alkyl groups or aromatic groups.
Description
Technical field
The present invention relates to a kind of diimidazole pyrazines derivatives and application thereof, be specifically related to a kind of diimidazole [1,2-a:2 ', 1 '-c] pyrazines derivatives and the application that this compounds is in electron transport material, organic electroluminescence device.
Background technology
The origin of organic electroluminescence device (OLED) can trace back to nineteen sixties, Pope et al. makes it luminous with anthracene single crystal impressed DC voltage, but because driving voltage high (100V) and luminosity and efficiency are all relatively low, it does not have cause too many attention. Along with technology is updated. at the C.W.Tang et al. of Kodak Company in 1987 with oxine aluminum (AIq3) for luminescent material, adopt the method for vacuum evaporation to be made for double layer sandwich structure OLED, open bright voltage and only have several volts, brightness reaches as high as 1000cd/m2, mark OLED has stepped an important step towards practical, becomes an important milestone of field of organic electroluminescence.
Electron transfer layer is requisite ingredient in organic electroluminescence device, as a rule, electron transport material all has the plane aromatic compound of big conjugated structure, they have good electron acceptability mostly, under certain forward bias, can effectively transmit again electronics (electroluminescent organic material and device introduction simultaneously, Huang Chunhui, Li Fuyou, Huang Wei, 143). It is currently available that electron transport material and mainly has oxine aluminum compounds, furodiazole compound, glyoxaline compound, oxazole compounds, triazole class compounds, nitrogenous hexa-member heterocycle class, perfluorinate electron-like transmission material, silicone based electron transport material etc.
Design an electron transport material that organic electroluminescence device efficiency can be made to be obviously improved, need to possess following character: there is reversible electrochemical reduction and higher reduction potential; Needing suitable HOMO and LUMO makes electronics have minimum injection energy gap, to reduce initial and operation voltage; Need higher electron mobility; The glass transition temperature having had and heat stability; There is noncrystalline thin film. (organic electroluminescent and element, Chen Jinxin, yellow filial piety literary composition work, 52 pages).
BPen (4,7-diphenyl-1,10-Phen) and BCP (2,9-dimethyl-4,7-diphenyl 1,-10-Phen) LUMO can rank at about 3.2ev, HOMO energy rank, at 6.5-6.7ev, are often used as OLED hole blocking layer, have higher electron mobility owing to it has firm planar structure, being disadvantageous in that this compounds Tg (glass transition temperature) is relatively low, being susceptible to decay during component operation affects the stability of assembly.(OLED illusion display-material and device, Chen Jinxin, yellow filial piety literary composition work, 53 pages).
Summary of the invention
The present inventor devises class 1,10-derivative of phenanthroline one diimidazole pyrazines derivatives, and by introducing different substituent groups on pyrazine, prepare a series of diimidazole [1,2-a:2 ', 1 '-c] and pyrazines derivatives and be applied to OLED preparation in, compared to 1,10-Phen, replace pyrazine and be easier to electron transmission, and there is better stability and film property, the device drive voltage prepared is lower, in hgher efficiency.
Diimidazole [1,2-a:2 ', 1 '-c] and pyrazines derivatives molecule be contained within multiple benzimidazole group, whole molecule is a big conjugate planes structure, these conjugate planes well improve electron mobility, and imidazole group has low reduction potential and is conducive to accepting electronics, thus being conducive to electric transmission, the charge transporting ability of this compounds can be improved, make it have good electronic transmission performance, the introducing of pyrazine structure further adds the electron deficiency ability of system, adds the compound ability to accept to electronics. Additionally, the symmetry of molecular structure can increase the regularity of molecular stacks, it is possible to improve compound carrier mobility. Meanwhile, the introducing of diimidazole [1,2-a:2 ', 1 '-c] pyrazine 5,6 bit substituent, well have adjusted the rigidity of compound, make product be more easy to film forming, improve the stability of device. Therefore this compound has higher electronic transmission performance, good film-forming property, at room temperature has good stability, and the device applied also has higher stability.
The present invention provides a kind of diimidazole pyrazines derivatives, and general structure is as follows:
Wherein, Ar is aromatic group, and R is the one in hydrogen, alkyl or aromatic group.
On the basis of technique scheme, the present invention can also do following improvement.
Further, described Ar be phenyl ring, naphthalene nucleus, furan nucleus, thiphene ring, pyridine ring, carbazole or containing substituent group above-mentioned aromatic group in one.
Further, described R is the one in hydrogen, methyl, cyano group, phenyl, 2-pyridine radicals, 3-pyridine radicals.
Further, the structural formula of described Ar is the one in following formula:
When Ar is above-mentioned substituent group, compound is easier to prepare, less costly, compound molecule has good carrier mobility, demonstrating good electronic transmission performance, the compound prepared has higher glass transition temperature, adds the stability of device.
The present invention also provides for the application of a kind of diimidazole pyrazines derivatives, in preparing organic electroluminescence device, has at least a functional layer, containing above-mentioned diimidazole pyrazines derivatives.
The present invention also provides for a kind of organic electroluminescence device, including the anode layer and the cathode layer that constitute pair of electrodes, and arrange in the electrodes luminescent layer and an electron transfer layer, and it is additionally provided with hole injection layer, hole transmission layer and/or electron injecting layer in the electrodes according to optional principle, wherein each layer presses the order arrangement of anode layer, hole injection layer, luminescent layer, electron transfer layer, electron injecting layer, cathode layer, connect in the way of plating between adjacent layer, forming laminated construction, the material of described electron transfer layer is selected from above-mentioned diimidazole pyrazines derivatives.
As previously mentioned, compound provided by the invention has higher electronic transmission performance, good film-forming property, at room temperature there is good stability, therefore driving voltage can be reduced, the feature of easy film forming makes manufacturing cost lower, and at room temperature stability makes device work more stable preferably, and physical life is longer.
Accompanying drawing explanation
Fig. 1 is the structural representation of a kind of simpler organic electroluminescence device provided by the invention.
1, glass substrate, 2, anode layer, 3, hole transmission layer, 4, luminescent layer, 5, electron transfer layer, 6, cathode layer.
Detailed description of the invention
For clearer explanation present disclosure, below in conjunction with the particular compound involved by technical solution of the present invention, set forth the present invention's by embodiment. It should be noted that embodiment does not limit the present invention for explaining.
For ease of quoting, by numeric suffix under the structural formula of above-mentioned each compound, and corresponding respectively with compound in preparation embodiment, such as, structural formula 1-1 correspondence prepares the compound 1-1 in embodiment one, and structural formula 1-2 correspondence prepares the compound 1-2 in embodiment two, and remaining is by that analogy.
Used alpha-brominated aromatic ketone in the present invention, replace the compound Chemical market at home such as diaminopyrazine, phenylboric acid, 2-pyridine boronic acid, 3-pyridine boronic acid and be commercially available.
Embodiment
The preparation of target compound, adopts alpha-brominated aromatic ketone and replaces diaminopyrazine under the catalysis of sodium bicarbonate, and in ethanol or DMF (DMF), cyclization prepares. Compound 1-35 to 1-85 adopts corresponding fragrance boric acid and 5,6-bis-bromo-2,9-disubstituted diimidazoles [1,2-a:2 ', 1 '-c] pyrazine employing coupling to prepare.
Preparation embodiment
The preparation of preparation embodiment one compound 1-1
11g (0.1mol) 2 is added successively in 1000mL there-necked flask, 3-diaminopyrazine, 44g (0.22mol) alpha-brominated 1-Phenylethanone., 84g sodium bicarbonate, 600g dehydrated alcohol, back flow reaction 10h, after reactant liquor sucking filtration, for faint yellow clarification, it is spin-dried for, adopt normal hexane and ethyl acetate (volume ratio normal hexane: ethyl acetate=4: 1) column chromatography, obtain 25.6g buff white solid, yield 82.5%.
Weighing 10g crude Compound 1-1, in vacuum sublimation instrument, distillation parameter is 2 �� 10 for distillation vacuum-5Pa, the three district's temperature that distil are 250 DEG C, and the two district's temperature that distil are 150 DEG C, and the district's temperature that distils is 60 DEG C, established temperature is gradient increased temperature, every 15min raises 10 DEG C, after being increased to target temperature, and insulation distillation 8h, distillation there are best quality compound 1-18.2g, distillation yield is 82%, and high resolution mass spectrum theoretical value is 311.1218, and test value is 311.1216.
The synthesis of preparation embodiment two compound 1-18
16g (0.1mol) 2,3-dicyano-4,5-diaminopyrazine is added successively in 1000mL there-necked flask, 44g (0.22mol) alpha-brominated 1-Phenylethanone., 84g sodium bicarbonate, 600g dehydrated alcohol, back flow reaction 18h, after reactant liquor sucking filtration, for faint yellow clarification, it is spin-dried for, adopts normal hexane and ethyl acetate (volume ratio normal hexane: ethyl acetate=4: 1) column chromatography, obtain 28.6g buff white solid, yield 79.4%.
Weighing 10g crude Compound 1-18, in vacuum sublimation instrument, distillation parameter is 2 �� 10 for distillation vacuum-5Pa, the three district's temperature that distil are 250 DEG C, and the two district's temperature that distil are 150 DEG C, and the district's temperature that distils is 60 DEG C, established temperature is gradient increased temperature, every 15min raises 10 DEG C, after being increased to target temperature, and insulation distillation 8h, distillation there are best quality compound 1-187.8g, distillation yield is 78%, and high resolution mass spectrum theoretical value is 361.3709, and test value is 361.3716.
The synthesis of preparation embodiment three compound 1-19
Adopting alpha-brominated 1-acetonaphthone and 2,3-cyano group-4,5-diaminopyrazine cyclization prepares compound 1-19, total recovery 65.6%, and high resolution mass spectrum theoretical value is 461.1436 test values is 461.1428.
The synthesis of preparation embodiment four compound 1-21
Adopting alpha-brominated 2-pyridine ethyl ketone and 2,3-cyano group-4,5-diaminopyrazine cyclization prepares compound 1-21, total recovery 60.6%, and high resolution mass spectrum theoretical value is 363.1028, and test value is 363.1022.
The synthesis of preparation embodiment five compound 1-33
Adopting alpha-brominated 4-(1-naphthyl) 1-Phenylethanone. and 2,3-cyano group-4,5-diaminopyrazine cyclization prepares compound 1-33, total recovery 58.6%, and high resolution mass spectrum theoretical value is 613.2062, and test value is 613.2056.
The synthesis of preparation embodiment six compound 1-35
26.8g (0.1mol) 2,3-bis-bromo-4,5-diaminopyrazine are added successively in 1000mL there-necked flask, 44g (0.22mol) alpha-brominated 1-Phenylethanone., 84g sodium bicarbonate, 600g dehydrated alcohol, back flow reaction 12h, after reactant liquor sucking filtration, for faint yellow clarification, it is spin-dried for, adopts normal hexane and ethyl acetate (volume ratio normal hexane: ethyl acetate=4: 1) column chromatography, obtain 30.6g buff white solid, yield 65.4%.
Then weigh 23.4g (0.05mol) 5 successively, 6-bis-bromo-2, 9-diphenyl diimidazole [1, 2-a:2 ', 1 '-c] and pyrazine, 13.3g (0.11mol) phenylboric acid, 200g toluene, 20.7g the solution of potassium carbonate and 100g water, after logical nitrogen 20min, add 600mg tetra-triphenylphosphine palladium, 80 DEG C of insulation 10h, separatory, reactant liquor 200g washes twice, organic facies adds 20g anhydrous sodium sulfate and is spin-dried for after drying, normal hexane and ethyl acetate (volume ratio normal hexane: ethyl acetate=1: 1) is then used to cross post, obtain 15.8g off-white color solid, yield 68.4%.
Weighing 10g crude Compound 1-35, in vacuum sublimation instrument, distillation parameter is 2 �� 10 for distillation vacuum-5Pa, the three district's temperature that distil are 290 DEG C, and the two district's temperature that distil are 190 DEG C, and the district's temperature that distils is 90 DEG C, established temperature is gradient increased temperature, every 15min raises 10 DEG C, after being increased to target temperature, and insulation distillation 8h, distillation there are best quality compound 1-358.8g, distillation yield is 88%, and high resolution mass spectrum theoretical value is 463.1844, and test value is 463.1846.
The synthesis of preparation embodiment seven compound 1-36
Adopt alpha-brominated 1-acetonaphthone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(1-naphthyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-36, total recovery 35.6%, high resolution mass spectrum theoretical value is 563.2157, and test value is 563.2156.
The synthesis of preparation embodiment eight compound 1-37
Adopt alpha-brominated 2-acetonaphthone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(2-naphthyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-37, total recovery 33.6%, high resolution mass spectrum theoretical value is 563.2157, and test value is 563.2156.
The synthesis of preparation embodiment nine compound 1-38
Adopt alpha-brominated 2-pyridine ethyl ketone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(2-pyridine radicals)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-38, total recovery 30.6%, high resolution mass spectrum theoretical value is 465.1749, and test value is 465.1746.
The synthesis of preparation embodiment ten compound 1-39
Adopt alpha-brominated 3-pyridine ethyl ketone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(3-pyridine radicals)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-39, total recovery 31.6%, high resolution mass spectrum theoretical value is 465.1749, and test value is 465.1746.
The synthesis of preparation embodiment 11 compound 1-40
Adopt alpha-brominated 4-pyridine ethyl ketone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-pyridine radicals)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-40, total recovery 34.8%, high resolution mass spectrum theoretical value is 465.1749, and test value is 465.1746.
The synthesis of preparation embodiment 12 compound 1-41
Adopt alpha-brominated-2-furan ethyl ketone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(2-furyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-41, total recovery 34.8%, high resolution mass spectrum theoretical value is 443.1430, and test value is 443.1426.
The synthesis of preparation embodiment 13 compound 1-42
Adopt alpha-brominated-2-furan ethyl ketone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(2-thienyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-42, total recovery 34.8%, high resolution mass spectrum theoretical value is 475.0973, and test value is 475.0966.
The synthesis of preparation embodiment 14 compound 1-43
Adopt alpha-brominated-4-nitro-acetophenone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-nitrobenzophenone)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-43, total recovery 32.7%, high resolution mass spectrum theoretical value is 553.1546, and test value is 553.1548.
The synthesis of preparation embodiment 15 compound 1-44
Adopt alpha-brominated-4-cyano-acetophenone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-cyano-phenyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-44, total recovery 31.7%, high resolution mass spectrum theoretical value is 513.1749, and test value is 513.1746.
The synthesis of preparation embodiment 16 compound 1-45
Adopt alpha-brominated-4-fluoro acetophenone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-fluorophenyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-45, total recovery 31.8%, high resolution mass spectrum theoretical value is 499.1656, and test value is 499.1648.
The synthesis of preparation embodiment 17 compound 1-46
Adopt alpha-brominated-4-methyl acetophenone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-aminomethyl phenyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-46, total recovery 31.8%, high resolution mass spectrum theoretical value is 491.2157, and test value is 491.2166.
The synthesis of preparation embodiment 18 compound 1-47
Adopt alpha-brominated-4-methoxyacetophenone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-methoxyphenyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-47, total recovery 30.3%, high resolution mass spectrum theoretical value is 523.2056, and test value is 523.2046.
The synthesis of preparation embodiment 19 compound 1-48
Adopt alpha-brominated-4-tert-butyl benzene ethyl ketone and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-tert-butyl-phenyl)-5,6-dibromo diimidazole [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-48, total recovery 25.3%, high resolution mass spectrum theoretical value is 575.3096, and test value is 575.3088.
The synthesis of preparation embodiment 20 compound 1-49
Adopt alpha-brominated-4-[9-carbazyl] 1-Phenylethanone. and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-[9-carbazyl] phenyl)-5,6-dibromo diimidazoles [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-49, total recovery 26.3%, high resolution mass spectrum theoretical value is 793.3001, and test value is 793.2998.
The synthesis of preparation embodiment 21 compound 1-50
Adopt alpha-brominated-4-[1-naphthyl] 1-Phenylethanone. and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-[1-naphthyl] phenyl)-5,6-dibromo diimidazoles [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-50, total recovery 24.6%, high resolution mass spectrum theoretical value is 715.2783, and test value is 715.2776.
The synthesis of preparation embodiment 22 compound 1-51
Adopt alpha-brominated-4-[2-naphthyl] 1-Phenylethanone. and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(4-[2-naphthyl] phenyl)-5,6-dibromo diimidazoles [1,2-a:2 ', 1 '-c] and pyrazine, then adopt phenylboric acid and its coupling to prepare compound 1-51, total recovery 22.8%, high resolution mass spectrum theoretical value is 715.2783, and test value is 715.2776.
The synthesis of preparation embodiment 23 compound 1-52
Adopt alpha-brominated 1-Phenylethanone. and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(phenyl)-5,6-dibromo diimidazoles [1,2-a:2 ', 1 '-c] and pyrazine, then adopt 2-pyridine phenylboric acid and its coupling to prepare compound 1-52, total recovery 27.3%, high resolution mass spectrum theoretical value is 465.1749, and test value is 465.1756.
The synthesis of preparation embodiment 24 compound 1-69
Adopt alpha-brominated 1-Phenylethanone. and 2,3-bis-bromo-4,5-diaminopyrazine cyclization prepares 2,9-bis-(phenyl)-5,6-dibromo diimidazoles [1,2-a:2 ', 1 '-c] and pyrazine, then adopt 3-pyridine phenylboric acid and its coupling to prepare compound 1-69, total recovery 28.6%, high resolution mass spectrum theoretical value is 465.1749, and test value is 465.1756.
The synthesis of preparation embodiment 25 compound 1-86
Adopting alpha-brominated 1-Phenylethanone. and 2,3-dimethyl-4,5-diaminopyrazine cyclization prepares compound 1-86, total recovery 68%, and high resolution mass spectrum theoretical value is 338.1531, and test value is 338.1526.
Device embodiments:
Device designs:
Here the first application for compound provided by the invention in the electron transfer layer of electroluminescent device, embodies its beneficial effect.
In order to conveniently compare the transmission performance of these electron transport materials, the present invention devises simple electroluminescent device. Wherein, compound 1-1,1-18,1-19,1-21,1-33,1-35,1-36,1-37,1-38,1-39,1-40,1-41,1-42,1-43,1-44,1-45,1-46,1-47,1-48,1-49,1-50,1-51,1-52,1-69,1-86 prepared by embodiment is prepared as electron transport material illustration using the present invention, efficent electronic transmission material Bphen is as comparing material, EM1 is as luminescent material illustration, with prominent compound provided by the invention at electroluminescent device, the especially beneficial effect in electron transport material.
The structure of Bphen and EM1 is as follows:
Selecting glass in the present invention is substrate, and ITO is anode material, and hole transmission layer the selection of material is NPB, and electron injecting layer material is LiF, and cathode material is Al.
(1) device manufacture
In conjunction with accompanying drawing 1, the glass plate supersound process in acetone of transparent conductive layer will be coated with, rinsing with in deionized water, at acetone: ultrasonic oil removing in dehydrated alcohol mixed solvent (mass ratio is 1: 1), it is baked under clean environment and completely removes moisture, by ultraviolet light and ozone clean, and with mental retardation positron bundle bombarded surface;
The above-mentioned glass substrate 1 with anode layer 2 is placed in vacuum chamber, is evacuated to 9x10-5Pa, on above-mentioned anode tunic, vacuum evaporation NPB is 0.05nm/s as hole transmission layer 3 evaporation rate, and evaporation thickness is 50nm;
On hole transmission layer 3, vacuum evaporation EM1 is as device luminescent layer 4, and evaporation rate is 0.05nm/s, and evaporation total film thickness is 40nm;
On luminescent layer 4, vacuum evaporation one stratification compound 1-1,1-18,1-19,1-21,1-33,1-35,1-36,1-37,1-38,1-39,1-40,1-41,1-42,1-43,1-44,1-45,1-46,1-47,1-48,1-49,1-50,1-51,1-52,1-69,1-86 or Bphen are as the electron transfer layer 5 of device, its evaporation rate is 0.05nm/s, and evaporation total film thickness is 30nm;
At the cathode layer 6 that the upper vacuum evaporation Al of electron transfer layer (ETL) is device, film thickness is 150nm.
Device performance is shown in following table (device architecture: ITO/NPB (50nm)/EM1 (40nm)/ETL (30nm)/LiF (0.5nm)/Al (150nm)).
Table 1
Above table result shows: compound provided by the invention, has more outstanding performance, it may be preferred to as electron transport layer materials in organic electroluminescent.
Generally, although have passed through embodiment and preferred implementation discloses the present invention, it should be appreciated that the invention is not restricted to disclosed embodiment. On the contrary, it will be understood by those skilled in the art that it is intended to various modification and similar arrangement. Therefore, scope of the following claims should be consistent to contain all such modification and similar arrangement with the widest explanation.
Claims (6)
1. a diimidazole pyrazines derivatives, it is characterised in that general structure is as follows:
Wherein, Ar is aromatic group, and R is the one in hydrogen, alkyl or aromatic group.
2. diimidazole according to claim 1 pyrazines derivatives, it is characterised in that described Ar be phenyl ring, naphthalene nucleus, furan nucleus, thiphene ring, pyridine ring, carbazole or containing substituent group above-mentioned aromatic group in one.
3. diimidazole according to claim 1 pyrazines derivatives, it is characterised in that described R is the one in hydrogen, methyl, cyano group, phenyl, 2-pyridine radicals, 3-pyridine radicals.
4. diimidazole according to claim 3 pyrazines derivatives, it is characterised in that the structural formula of described Ar is the one in following formula:
5. the application of a diimidazole pyrazines derivatives, it is characterised in that in preparing organic electroluminescence device, has at least a functional layer, containing the arbitrary described diimidazole of claim 1-4 pyrazines derivatives.
6. an organic electroluminescence device, it is characterized in that, including the anode layer and the cathode layer that constitute pair of electrodes, and arrange in the electrodes luminescent layer and an electron transfer layer, and it is additionally provided with hole injection layer in the electrodes according to optional principle, hole transmission layer and/or electron injecting layer, each layer presses anode layer, hole injection layer, luminescent layer, electron transfer layer, electron injecting layer, the order arrangement of cathode layer, connect in the way of plating between adjacent layer, form laminated construction, the material of described electron transfer layer is selected from the arbitrary described diimidazole of claim 1-4 pyrazines derivatives.
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| CN109180690A (en) * | 2018-10-15 | 2019-01-11 | 烟台显华化工科技有限公司 | One kind is used as azepine aromatic compound and its application of blue fluorescent material |
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