CN102827196B - Boron-containing indole (3, 2-b) carbazole derivative and preparion method and application thereof - Google Patents
Boron-containing indole (3, 2-b) carbazole derivative and preparion method and application thereof Download PDFInfo
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Abstract
The invention provides a boron-containing indole (3, 2-b) carbazole derivative, in particular to 2, 8-2(trimethylphenyl boron)-5, 11-dialkyl indole (3, 2-b) carbazole. A preparation method of the boron-containing indole (3, 2-b) carbazole derivative comprises the steps of: sequentially preparing cyclohexane-1, 4-diketone-2 (4-bromobenzene) hydrazone, 2, 8-dibromo-indole (3, 2-b) carbazole and 2, 8-dibromo-5, 11-dialkyl indole (3, 2-b) carbazole; and then, leading the 2, 8-dibromo-5, 11-dialkyl indole (3, 2-b) carbazole to have reaction with 2(trimethylphenyl) boron fluoride to obtain the 2, 8-2(trimethylphenyl boron)-5, 11-dialkyl indole (3, 2-b) carbazole. The boron-containing indole (3, 2-b) carbazole derivative is good in stability and can be used as blue organic electroluminescent material.
Description
One, technical field
The present invention relates to the heterogeneous ring compound of carbon containing, hydrogen, nitrogen, boron, specifically belong to a kind of boracic indoles [3,2-b] carbazole derivative and preparation method thereof, this derivative can be used as blue organic electroluminescent material.
Two, background technology
After entering 21 century, the performance of sustained and rapid development to information display system of information technology proposes high requirement, in order to meet the information age to gentlier, the high performance flat display part that thinner, visual angle is wider in the urgent need to, organic electroluminescence device (OLED) arises at the historic moment as the flat panel display of a new generation and progresses into the visual field of people, its application prospect and in recent years advancing by leaps and bounds and make OLED become one of the most popular topic of field of information display technically widely.
Organic materials has higher fluorescence quantum efficiency, by " assembling " and " cutting " to organic molecule, can design the organic molecule that can provide various glow color.These advantages and indicate powerfully excite exploitation and the applied research that people are devoted to electroluminescent organic material enormously potentially.
Indoles [3,2-b] carbazole is a kind of ladder shape planar compound with large π-electron-conjugated system, has excellent thermostability.Hydrogen on this compound 5,11,2,8 or 3,9 is easily replaced formation derivative by many functional groups.Indoles [3,2-b] carbazole derivative has excellent thermostability and photoelectric property, has broad application prospects in organic electroluminescent light, electroluminescent, nonlinear optical material etc.
Triarylborane is the important organic compound of a class, they solution and solid-state in all there is high luminous efficiency, these compounds are had a wide range of applications at photoelectric fields such as Organic Light Emitting Diodes (OLEDs).
Three, summary of the invention
The object of the present invention is to provide a kind of boracic indoles [3,2-b] carbazole derivative, the preparation method of this derivative is provided, and provides this derivative as the electroluminescent device of blue organic electroluminescent material.
A kind of boracic indoles [3,2-b] carbazole derivative provided by the invention, be 2,8-bis-(trimethylphenyl boron)-5,11-Dialkyl indol [3,2-b] carbazole, its molecular structure is:
R is CH
2cH
3, C
3h
7, C
4h
9, C
5h
11, C
6h
13, C
8h
17or C
6h
5.
The preparation method of a kind of boracic indoles [3,2-b] carbazole derivative provided by the invention, reaction formula is as follows:
Preparation process comprises:
(1) 1:2 gets Isosorbide-5-Nitrae-cyclohexanedione and 4-bromophenyl-hydrazine hydrochloride in molar ratio; Dropwise being joined by the Isosorbide-5-Nitrae-cyclohexanedione being dissolved in dehydrated alcohol is dissolved in the 4-bromophenyl-hydrazine hydrochloride of dehydrated alcohol; When 60 ° of C, react 2 hours; Through suction filtration, after washing, obtain hexahydroaniline-Isosorbide-5-Nitrae-diketone-two (4-bromobenzene) hydrazone;
(2) by hexahydroaniline-Isosorbide-5-Nitrae-diketone-two (4-bromobenzene) hydrazone solid, under condition of ice bath, Glacial acetic acid is slowly joined and vitriol oil volume ratio is in the mixed solution of 4:1; Heat up subsequently, react 10 hours when 80 ° of C; Poured into by reaction solution in frozen water, have a large amount of solid to separate out immediately, suction filtration after fully stirring, obtains thick product; After washing and ethanol are washed, obtain greenish yellow solid, be 2,8-bis-bromo indole [3,2-b] carbazole;
(3) 1:3:3 gets 2,8-bis-bromo indole [3,2-b] carbazole, NaH and bromoalkane in molar ratio; 2,8-bis-bromo indole [3,2-b] carbazole is dissolved in tetrahydrofuran solvent, when 0 ° of C, adds NaH; React 1 hour, then raised temperature; When 60 ° of C, react 10 hours; Then be cooled to room temperature, add bromoalkane; At room temperature, react 24 hours; Except desolventizing, wash with water, obtain 2,8-bis-bromo-5,11-Dialkyl indol [3,2-b] carbazole;
(4) 1:2.3-2.5:2.5-3.0 gets 2,8-bis-bromo-5,11-Dialkyl indol [3,2-b] carbazole, n-Butyl Lithium and two (trimethylphenyl) boron fluoride in molar ratio; By 2,8-bis-bromo-5,11-Dialkyl indol [3,2-b] carbazole is dissolved in anhydrous tetrahydro furan solvent, when-78 ° of C, add n-Butyl Lithium, recover room temperature after stirring 20min at this temperature, and then the anhydrous tetrahydrofuran solution that will be dissolved with two (trimethylphenyl) boron fluoride after being down to-78 ° of C instills wherein, stir after recovering room temperature and spend the night, rotary evaporation is except desolventizing afterwards, gained solid ether and water washing, obtain 2,8-bis-(trimethylphenyl boron)-5 after drying, 11-Dialkyl indol [3,2-b] carbazole.
The mol ratio of described 2,8-bis-bromo-5,11-Dialkyl indol [3,2-b] carbazoles, n-Butyl Lithium and two (trimethylphenyl) boron fluoride is 1.0:2.5:3.0.
The present invention separately provides a kind of electroluminescent device, comprises luminescent layer, and described luminescent layer contains described boracic indoles [3,2-b] carbazole derivative.
A kind of electroluminescent device provided by the invention, comprises luminescent layer, and described luminescent layer is the coating of boracic indoles [3,2-b] carbazole derivative.
The concrete structure of electroluminescent device is: ITO/NPB (40nm)/BCP(10nm)/2,8-bis-(trimethylphenyl boron)-5,11-Dialkyl indol [3,2-b] carbazole (30nm)/Bphen (40nm)/LiF (0.5nm)/Al (150nm).Wherein NPB is as hole mobile material, and BCP is as hole barrier materials, and Bphen is as electron transport material.
The preparation method of luminescent device of the present invention, comprises the following steps:
Cleaning ito glass, first cleans ito glass with acetone, then, rinses, then use scavenging solution ultrasonic cleaning again, then wash with clear water is ultrasonic with clear water.The substrate nitrogen cleaned dries up, finally surperficial fully to clean with ultraviolet-ozone process.According to the structure hole mobile material NPB that evaporation 40nm is thick on ITO substrate successively in order of designed device; Evaporation BCP is as hole barrier materials; Then the luminescent material of the present invention 2,8-bis-(trimethylphenyl boron)-5,11-Dialkyl indol [3,2-b] carbazole (material of main part) that evaporation 40nm is thick is as luminescent layer; Then the Bphen that evaporation 40nm is thick is as electron transfer layer, and the lithium fluoride that finally evaporation 0.5nm is thick successively and the thick aluminium of 150nm are as the negative electrode of device.
Whole evaporate process is carried out all under a high vacuum, the evaporation rate of organic layer (NPB, BCP, material of main part and Bphen) controls at 0.2-0.5nm/s, and the evaporation speed control of metallic aluminum is all undertaken monitoring and detecting by quartz resonator built in the thickness of 0.5-1nm/s. film and sedimentation rate.
The performance test results of luminescent device provided by the invention: galvanic positive pole is added on ITO layer, negative pole is added on LiF/Al layer, namely from the uniform blue light of ITO layer emitting bright, glow peak is at 440nm, and peak width at half height is 64nm, CIE coordinate is (0.125,0.075), trigger voltage 3.6V, when voltage is 5.5V, reaches high-high brightness 5342cd/m
2, maximum current efficiency is 1.25cd/A.Electroluminescent device test result shows that boracic indoles [3,2-b] carbazole derivative of the present invention has excellent electroluminescent properties as luminescent material, has wide application prospect.
Described boracic indoles [3,2-b] carbazole derivative is 2,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole.
Compared with prior art, the advantage that has of the present invention and effect:
1. boron indoles [3, the 2-b] carbazole derivative of the present invention's synthesis, has Heat stability is good, the feature that luminous efficiency is high, can be used as luminescent material.
2. the simple synthetic method of boron indoles [3,2-b] carbazole derivative provided by the invention, products collection efficiency and purity high, operate easy.
3. boron indoles [3,2-b] carbazole derivative provided by the invention can be used as the blue emitting material in organic electroluminescence device, has broad application prospects.
Four, accompanying drawing explanation
The hydrogen nuclear magnetic resonance spectrogram of Figure 12,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole
The carbon-13 nmr spectra figure of Figure 22,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole
The mass spectrum of Figure 32,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole
The thermogravimetric analysis figure of Figure 42,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole
The ultra-violet absorption spectrum of Figure 52,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole in THF
The fluorescence spectrum figure of Figure 62,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole in THF
The structural representation of Fig. 7 luminescent device
The current-voltage-brightness curve of the device of Figure 82,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole
The electroluminescent EL spectrum of device under different driving voltage of Figure 92,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole
Five, embodiment
The preparation of embodiment 12,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole, step is as follows:
(1) synthesis of hexahydroaniline-Isosorbide-5-Nitrae-diketone-two (4-bromobenzene) hydrazone
At room temperature, get 5.62g(50mmol) 1,4-cyclohexanedione is dissolved in 100ml dehydrated alcohol, be made into 1,4-cyclohexanedione ethanolic soln, is slowly added drop-wise to above-mentioned solution constant pressure funnel and is dissolved with 22.4g(100mmol under fully stirring) 4-bromophenyl-hydrazine hydrochloride and 8.2g(100mmol) sodium acetate, anhydrous 200ml ethanol solution in.After dropwising, rapid temperature increases to 50 ° C, reacts 2 hours.Reaction solution is cooled to 0 ° of C, washes and drying through suction filtration, washing, ethanol, obtain 15.7g faint yellow solid.Productive rate is 76%.
The synthesis of (2) 2,8-bis-bromo indole [3,2-b] carbazoles
By 10g(22mmol) hexahydroaniline-Isosorbide-5-Nitrae-diketone-two (4-bromobenzene) hydrazone solid slowly joins in 0 ° of C mixing solutions of 130mL Glacial acetic acid and the 32mL vitriol oil.Stirring reaction 1 hour, is warming up to 30 ° of C subsequently and reacts 1 hour, then is warming up to 60-70 ° of C and reacts 2 hours.Reaction solution is cooled to room temperature, pours in frozen water, separate out solid.Wash and drying through suction filtration, washing, ethanol, obtain 4.62g yellow-green colour compound.Productive rate is 50%.
The synthesis of bromo-5,11-di-n-butyl indoles [3, the 2-b] carbazoles of (3) 2,8-bis-
Under nitrogen protection, by 4.14g(10mmol) 2,8-bis-dry bromo indole [3,2-b] carbazoles are dissolved in the tetrahydrofuran solvent of 100ml.Under nitrogen protection, add 0.72g(30mmol) NaH, at room temperature, reacts 2 hours.Slowly be warming up to 50 ° of C, at this temperature, react 4 hours.Reaction solution is cooled to room temperature, adds 4.09g(30mmol) 1-bromine normal hexane.Room temperature reaction 1 hour, and then be warming up to 50 ° of C, at this temperature, react 24 hours.After reaction terminates, solvent is steamed, the solids washed with water obtained 2-3 time, finally obtain 4.64g yellow compound with washing with acetone.Productive rate is 80%.
The synthesis of (4) 2,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazoles
Under nitrogen protection by the 0.44g(0.84mmol of drying) 2, 8-bis-bromo-5, 11-di-n-butyl indoles [3, 2-b] carbazole, be added in schlenk bottle, then add 50ml anhydrous tetrahydro furan and solution liquid nitrogen acetone bath is chilled to-78 ° of C, add the n-Butyl Lithium hexane solution of 0.8ml 2.5mol/L afterwards, room temperature is recovered after stirring 20min at this temperature, and then will 0.67g(2.5mmol be dissolved with after being down to-78 ° of C) instillation of the 20ml anhydrous tetrahydrofuran solution of two (trimethylphenyl) boron fluoride is wherein, stir after recovering room temperature and spend the night, rotary evaporation is except desolventizing afterwards, gained solid ether and water washing, 0.23g 2 is obtained after drying, 8-bis-(trimethylphenyl boron)-5, 11-di-n-butyl indoles [3, 2-b] carbazole.Product is white powder, and productive rate is 32%.Product characterization result is shown in Fig. 1-6.
The structure of embodiment 2 electroluminescent device, preparation and performance:
The structure of luminescent device as shown in Figure 7.
The making step of electroluminescent device:
Cleaning ito glass, first cleans ito glass with acetone, then, rinses, then use scavenging solution ultrasonic cleaning again, then wash with clear water is ultrasonic with clear water.The substrate nitrogen cleaned dries up, finally surperficial fully to clean with ultraviolet-ozone process.According to the structure of device in order successively on ITO substrate vacuum evaporation NPB as hole mobile material; Evaporation BCP is as hole barrier materials; 2,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole is as luminescent layer; Bphen is as electron transfer layer, and lithium fluoride is as electron injecting layer, and aluminium is as the negative electrode of device.In device, the thickness of each material is: NPB, 40nm; BCP, 10nm; 2,8-bis-(trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole, 40nm; Bphen 40nm; LiF, 0.5nm; Al, 150nm.
The performance of electroluminescent device:
Galvanic positive pole is added on ITO layer, negative pole is added on LiF/Al layer, namely from the uniform blue light of ITO layer emitting bright, glow peak is at 440nm, peak width at half height is 64nm, CIE coordinate is (0.125,0.075), trigger voltage 3.6V, when voltage is 5.5V, reaching high-high brightness is 5342cd/m
2, maximum current efficiency is 1.25cd/A.Electroluminescent device result shows that luminescent material of the present invention has excellent electroluminescent properties.Test result is shown in Fig. 8 and Fig. 9.
Claims (7)
1. boracic indoles [3, a 2-b] carbazole derivative, its molecular structural formula is:
R is CH
2cH
3, C
3h
7, C
4h
9, C
5h
11, C
6h
13, C
8h
17.
2. a kind of boracic indoles [3 as claimed in claim 1,2-b] preparation method of carbazole derivative, comprise the steps: that 1.0:2.3-2.5:2.5-3.0 gets 2 in molar ratio, 8-bis-bromo-5,11-Dialkyl indol [3,2-b] carbazole, n-Butyl Lithium and two (trimethylphenyl) boron fluoride; By 2,8-bis-bromo-5,11-Dialkyl indol [3,2-b] carbazole is dissolved in tetrahydrofuran solvent,-78 DEG C time, add n-Butyl Lithium, stir after 20min at this temperature and recover room temperature, and then be down to the anhydrous tetrahydrofuran solution that will be dissolved with two (trimethylphenyl) boron fluoride after-78 DEG C and instill wherein, stir after recovering room temperature and spend the night, rotary evaporation is except desolventizing afterwards, gained solid ether and water washing, obtains object product after drying.
3. a kind of boracic indoles [3 as claimed in claim 2,2-b] preparation method of carbazole derivative, it is characterized in that, described 2,8-bis-bromo-5, the mol ratio of 11-Dialkyl indol [3,2-b] carbazole, n-Butyl Lithium and two (trimethylphenyl) boron fluoride is 1.0:2.5:3.0.
4. an electroluminescent device, comprises luminescent layer, it is characterized in that described luminescent layer contains boracic indoles [3,2-b] carbazole derivative according to claim 1.
5. an electroluminescent device, comprises luminescent layer, it is characterized in that described luminescent layer is the coating of boracic indoles [3,2-b] carbazole derivative according to claim 1.
6. the manufacture method of a kind of electroluminescent device as claimed in claim 5, is characterized in that comprising the following steps: cleaning ito glass, and nitrogen dries up, and finally reaches the surface fully cleaned with ultraviolet-ozone process; According to the structure NPB that evaporation 40nm is thick on ITO substrate successively in order of designed device, BCP that evaporation 10nm is thick; Boracic indoles [3, the 2-b] carbazole derivative of structure described in the claim 1 that evaporation 40nm is thick as the thick Bphen of luminescent layer, evaporation 40nm as the thick lithium fluoride of electron transfer layer, evaporation 0.5nm and the thick aluminium of the 150nm negative electrode as device.
7. the manufacture method of a kind of electroluminescent device as claimed in claim 6, it is characterized in that described whole evaporate process is carried out all under a high vacuum, the evaporation rate of organic layer controls at 0.2-0.5nm/s, and the evaporation speed control of metallic aluminum is built in 0.5-1nm/s.
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| TWI599570B (en) * | 2012-09-28 | 2017-09-21 | 新日鐵住金化學股份有限公司 | Compounds for organic electroluminescent devices and organic electroluminescent devices |
| CN105009316B (en) * | 2013-02-28 | 2017-03-08 | 新日铁住金化学株式会社 | Organic electric-field light-emitting element boron compound and organic electric-field light-emitting element |
| CN103483364A (en) * | 2013-09-03 | 2014-01-01 | 太仓碧奇新材料研发有限公司 | Bis-benzothiophene borane luminescent material and preparation method thereof |
| CN103483365B (en) * | 2013-09-03 | 2016-04-27 | 太仓碧奇新材料研发有限公司 | A kind of also three thiophene borine transistor materials and preparation method thereof |
| CN103626792B (en) * | 2013-11-27 | 2015-10-21 | 山西大学 | A kind of indoles [3,2-b] carbazole compound containing aryl boron and Synthesis and applications thereof |
| CN104604893A (en) * | 2014-12-31 | 2015-05-13 | 江阴苏利化学股份有限公司 | Carbazole-containing pesticide composition for controlling brevicoryne brassicae |
| CN104430408A (en) * | 2014-12-31 | 2015-03-25 | 江阴苏利化学股份有限公司 | New application of pesticide composite containing carbazole and used for preventing and treating cabbage aphides |
| CN109485665A (en) * | 2017-09-13 | 2019-03-19 | 北京鼎材科技有限公司 | Compound and application thereof and organic electroluminescence device |
| CN109535187A (en) * | 2017-09-22 | 2019-03-29 | 北京鼎材科技有限公司 | Compound and application thereof and organic electroluminescence device |
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