CN102827196A - 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 verivate can be used as blue organic electroluminescent material.
Two, background technology
Get into after 21 century; The sustained and rapid development of infotech has proposed high requirement to the performance of information display system; For satisfy the information age to gentlier, the pressing for of thinner, high-performance flat-panel display device that the visual angle is wider; Organic electroluminescence device (OLED) arises at the historic moment as the flat panel display of a new generation and progresses into people's the visual field, its application prospects and advancing by leaps and bounds and make OLED become one of the most popular topic of field of information display technically in recent years.
Organic materials has higher fluorescence quantum efficiency, can design the organic molecule that various glow colors can be provided through " assembling " and " cutting " to organic molecule.These advantages and powerful exploitation and the applied research that has excited people to be devoted to electroluminescent organic material that is indicated thereof enormously potentially.
Indoles [3,2-b] carbazole is a kind of ladder shape complanation compound with big π-electron conjugated system, and good thermostability is arranged.Hydrogen on 5,11,2,8 or 3,9 of this compounds is replaced by many functional groups easily and forms verivates.Indoles [3,2-b] carbazole derivative has good thermostability and photoelectric property, has broad application prospects at aspects such as organic electroluminescent light, electroluminescent, nonlinear optical materials.
Triarylborane is one type of important organic cpds, they solution and solid-state in all have high luminous efficiency, make these compounds have a wide range of applications at Organic Light Emitting Diode photoelectric fields such as (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 verivate is provided, and the electroluminescent device of this verivate as blue organic electroluminescent material is provided.
A kind of boracic indoles provided by the invention [3,2-b] carbazole derivative is 2,8-two (trimethylphenyl boron)-5, and 11-dialkyl group indoles [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 provided by the invention [3,2-b] carbazole derivative, reaction formula is following:
Preparation process comprises:
(1) 1:2 gets 1 in molar ratio, 4-cyclohexanedione and 4-bromophenyl-hydrazine hydrochloride; To be dissolved in 1 of absolute ethyl alcohol, the 4-cyclohexanedione dropwise joins in the 4-bromophenyl-hydrazine hydrochloride that is dissolved in absolute ethyl alcohol; When 60 ° of C, reacted 2 hours; Through suction filtration, after the washing, obtain hexahydroaniline-1,4-diketone-two (4-bromobenzene) hydrazone;
(2) with hexahydroaniline-1,4-diketone-two (4-bromobenzene) hydrazone solid, under condition of ice bath, slowly joining Glacial acetic acid min. 99.5 and vitriol oil volume ratio is in the mixed solution of 4:1; Heat up subsequently, reaction is 10 hours when 80 ° of C; Reaction solution is poured in the frozen water, had a large amount of solids to separate out immediately, fully stir the back suction filtration, obtain thick product; Through washing with after ethanol washes, obtain the yellow-green colour solid, be 2,8-two bromo indoles [3,2-b] carbazole;
(3) 1:3:3 gets 2 in molar ratio, 8-two bromo indoles [3,2-b] carbazole, NaH and bromoalkane; With 2,8-two bromo indoles [3,2-b] carbazole is dissolved in the tetrahydrofuran solvent, when 0 ° of C, adds NaH; Reacted 1 hour, then elevated temperature; When 60 ° of C, reacted 10 hours; Be cooled to room temperature then, add bromoalkane; At room temperature, reaction is 24 hours; Remove and desolvate, use water washing, obtain 2,8-two bromo-5,11-dialkyl group indoles [3,2-b] carbazole;
(4) 1:2.3-2.5:2.5-3.0 gets 2 in molar ratio, 8-two bromo-5,11-dialkyl group indoles [3,2-b] carbazole, n-Butyl Lithium and two (trimethylphenyl) boron fluoride; With 2,8-two bromo-5,11-dialkyl group indoles [3; 2-b] carbazole is dissolved in the anhydrous tetrahydro furan solvent, when-78 ° of C, adds n-Butyl Lithium; After stirring 20min under this temperature, recover room temperature, and then reducing to the anhydrous tetrahydrofuran solution that will be dissolved with two (trimethylphenyl) boron fluoride behind-78 ° of C and splash into wherein, recovering stirred overnight after the room temperature; Rotary evaporation removes and desolvates afterwards, and the gained solid gets 2 with ether and water washing after the drying; 8-two (trimethylphenyl boron)-5,11-dialkyl group indoles [3,2-b] carbazole.
Described 2,8-two bromo-5, the mol ratio of 11-dialkyl group indoles [3,2-b] carbazole, n-Butyl Lithium and two (trimethylphenyl) boron fluoride is 1.0:2.5:3.0.
The present invention provides a kind of electroluminescent device in addition, 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-two (trimethylphenyl boron)-5,11-dialkyl group indoles [3,2-b] carbazoles (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 may further comprise the steps:
Clean ito glass, clean ito glass with acetone earlier, then, use flushing with clean water, then use the scavenging solution ultrasonic cleaning again, wash with clear water is ultrasonic again.The substrate of cleaning dries up with nitrogen, and is surperficial fully to clean with ultraviolet ray-ozonize at last.The structure hole mobile material NPB that vapor deposition 40nm is thick on the ITO substrate successively in order according to the device that is designed; Vapor deposition BCP is as hole barrier materials; The thick luminescent material of the present invention 2 of vapor deposition 40nm then, 8-two (trimethylphenyl boron)-5,11-dialkyl group indoles [3,2-b] carbazoles (material of main part) are as luminescent layer; The Bphen that vapor deposition 40nm is thick then is as electron transfer layer, and the thick aluminium of last lithium fluoride that vapor deposition 0.5nm is thick successively and 150nm is as the negative electrode of device.
Whole evaporate process is all carried out under high vacuum; The evaporation rate of organic layer (NPB, BCP, material of main part and Bphen) is controlled at 0.2-0.5nm/s, and the vapor deposition speed control of metal aluminium lamination is all monitored and detected through quartz resonator built in the thickness and the sedimentation rate of 0.5-1nm/s. film.
The The performance test results of luminescent device provided by the invention: galvanic positive pole is added on the ITO layer, negative pole is added on the LiF/Al layer, promptly from the uniform blue light of ITO layer emitting bright; Glow peak is at 440nm, and peak width at half is 64nm, and the 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 efficient is 1.25cd/A.The electroluminescent device test result shows that boracic indoles of the present invention [3,2-b] carbazole derivative has good electroluminescent properties as luminescent material, has wide application prospect.
Described boracic indoles [3,2-b] carbazole derivative is 2,8-two (trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole.
Compared with prior art, the advantage and the effect that have of the present invention:
1. synthetic boron indoles of the present invention [3,2-b] carbazole derivative has Heat stability is good, and the characteristics that luminous efficiency is high can be used as luminescent material.
2. the simple synthetic method of boron indoles provided by the invention [3,2-b] carbazole derivative, product productive rate and purity are high, and operation is prone to row.
3. boron indoles provided by the invention [3,2-b] carbazole derivative can be used as the blue emitting material in the organic electroluminescence device, has broad application prospects.
Four, description of drawings
Figure 12,8-two (trimethylphenyl boron)-5, the hydrogen nuclear magnetic resonance spectrogram of 11-di-n-butyl indoles [3,2-b] carbazole
Figure 22,8-two (trimethylphenyl boron)-5, the carbon-13 nmr spectra figure of 11-di-n-butyl indoles [3,2-b] carbazole
Figure 32,8-two (trimethylphenyl boron)-5, the mass spectrum of 11-di-n-butyl indoles [3,2-b] carbazole
Figure 42,8-two (trimethylphenyl boron)-5, the thermogravimetric analysis figure of 11-di-n-butyl indoles [3,2-b] carbazole
Figure 52,8-two (trimethylphenyl boron)-5, the uv absorption spectrum of 11-di-n-butyl indoles [3,2-b] carbazole in THF
Figure 62,8-two (trimethylphenyl boron)-5, the fluorescence spectrum figure of 11-di-n-butyl indoles [3,2-b] carbazole in THF
The structural representation of Fig. 7 luminescent device
Figure 82,8-two (trimethylphenyl boron)-5, the current-voltage-brightness curve of the device of 11-di-n-butyl indoles [3,2-b] carbazole
Figure 92,8-two (trimethylphenyl boron)-5, the electroluminescent EL spectrum of device under different driving voltage of 11-di-n-butyl indoles [3,2-b] carbazole
Five, embodiment
Embodiment 12,8-two (trimethylphenyl boron)-5, and the preparation of 11-di-n-butyl indoles [3,2-b] carbazole, step is following:
(1) hexahydroaniline-1,4-diketone-two (4-bromobenzene) hydrazone synthetic
At room temperature; Get 1 of 5.62g (50mmol); The 4-cyclohexanedione is dissolved in the 100ml absolute ethyl alcohol; Be made into 1,4-cyclohexanedione ethanolic soln slowly is added drop-wise to above-mentioned solution with constant pressure funnel in the 200ml ethanol solution that is dissolved with 22.4g (100mmol) 4-bromophenyl-hydrazine hydrochloride and 8.2g (100mmol) sodium acetate, anhydrous under fully stirring.After dropwising, be warming up to 50 ° of C rapidly, reacted 2 hours.Reaction solution is cooled to 0 ° of C, washes and drying, obtain the 15.7g faint yellow solid through suction filtration, washing, ethanol.Productive rate is 76%.
Synthesizing of (2) 2,8-two bromo indoles [3,2-b] carbazole
With 10g (22mmol) hexahydroaniline-1,4-diketone-two (4-bromobenzene) hydrazone solid slowly joins in 0 ° of C mixing solutions of the 130mL Glacial acetic acid min. 99.5 and the 32mL vitriol oil.Stirring reaction 1 hour is warming up to 30 ° of C reactions 1 hour subsequently, is warming up to 60-70 ° of C reaction 2 hours again.Reaction solution is cooled to room temperature, pours in the frozen water, separate out solid.Wash and drying through suction filtration, washing, ethanol, obtain 4.62g yellow-green colour compound.Productive rate is 50%.
(3) 2,8-two bromo-5,11-di-n-butyl indoles [3,2-b] carbazole synthetic
Under nitrogen protection, with 4.14g (10mmol) exsiccant 2,8-two bromo indoles [3,2-b] carbazole is dissolved in the tetrahydrofuran solvent of 100ml.Under nitrogen protection, add 0.72g (30mmol) NaH, at room temperature, reacted 2 hours.Slowly be warming up to 50 ° of C, under this temperature, reacted 4 hours.Reaction solution is cooled to room temperature, adds the 1-bromine normal hexane of 4.09g (30mmol).Room temperature reaction 1 hour, and then be warming up to 50 ° of C, under this temperature, reacted 24 hours.Reaction after finishing steams solvent, with water washing 2-3 time, obtains the 4.64g yellow compound to the solid that obtains with washing with acetone at last.Productive rate is 80%.
(4) 2,8-two (trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole synthetic
Under nitrogen protection with exsiccant 0.44g (0.84mmol) 2,8-two bromo-5,11-di-n-butyl indoles [3; 2-b] carbazole, be added in the schlenk bottle, add the 50ml anhydrous tetrahydro furan then and solution is chilled to-78 ° of C with the liquid nitrogen acetone bath; The n-Butyl Lithium hexane solution that adds 0.8ml 2.5mol/L is afterwards recovering room temperature after stirring 20min under this temperature, and then reduces to the 20ml anhydrous tetrahydrofuran solution that will be dissolved with 0.67g (2.5mmol) two (trimethylphenyl) boron fluoride behind-78 ° of C and splash into wherein; Stirred overnight after the recovery room temperature, rotary evaporation removes and desolvates afterwards, and the gained solid is with ether and water washing; Obtain 0.23g 2 after the drying; 8-two (trimethylphenyl boron)-5,11-di-n-butyl indoles [3,2-b] carbazole.Product is a white powder, and productive rate is 32%.The product characterization result is seen Fig. 1-6.
Structure, preparation and the performance of embodiment 2 electroluminescent devices:
The structure of luminescent device is as shown in Figure 7.
The making step of electroluminescent device:
Clean ito glass, clean ito glass with acetone earlier, then, use flushing with clean water, then use the scavenging solution ultrasonic cleaning again, wash with clear water is ultrasonic again.The substrate of cleaning dries up with nitrogen, and is surperficial fully to clean with ultraviolet ray-ozonize at last.According to the structure of device in order successively on the ITO substrate vacuum evaporation NPB as hole mobile material; Vapor deposition BCP is as hole barrier materials; 2,8-two (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.The thickness of each material is in the device: NPB, 40nm; BCP, 10nm; 2,8-two (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 the ITO layer, negative pole is added on the LiF/Al layer, promptly from the uniform blue light of ITO layer emitting bright, glow peak is at 440nm; Peak width at half is 64nm, and the CIE coordinate is (0.125,0.075); Trigger voltage 3.6V, when voltage was 5.5V, reaching high-high brightness was 5342cd/m
2, maximum current efficient is 1.25cd/A.The electroluminescent device result shows that luminescent material of the present invention has good electroluminescent properties.Test result is seen Fig. 8 and Fig. 9.
Claims (7)
1. a boracic indoles [3,2-b] carbazole derivative is 2,8-two (trimethylphenyl boron)-5, and 11-dialkyl group indoles [3,2-b] carbazole, its molecular structural formula is:
R is CH
2CH
3, C
3H
7, C
4H
9, C
5H
11, C
6H
13, C
8H
17Or C
6H
5
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-two bromo-5; 11-dialkyl group indoles [3,2-b] carbazole, n-Butyl Lithium and two (trimethylphenyl) boron fluoride; With 2,8-two bromo-5,11-dialkyl group indoles [3; 2-b] carbazole is dissolved in the tetrahydrofuran solvent, when-78 ° of C, adds n-Butyl Lithium; After stirring 20min under this temperature, recover room temperature, and then reducing to the anhydrous tetrahydrofuran solution that will be dissolved with two (trimethylphenyl) boron fluoride behind-78 ° of C and splash into wherein, recovering stirred overnight after the room temperature; Rotary evaporation removes and desolvates afterwards, and the gained solid gets 2 with ether and water washing after the drying; 8-two (trimethylphenyl boron)-5,11-dialkyl group indoles [3,2-b] carbazole.
3. the preparation method of a kind of boracic indoles as claimed in claim 2 [3,2-b] carbazole derivative is characterized in that; Described 2; 8-two bromo-5, the mol ratio of 11-dialkyl group indoles [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 the described boracic indoles of claim 1 [3,2-b] carbazole derivative.
5. an electroluminescent device comprises luminescent layer, it is characterized in that described luminescent layer is the coating of the described boracic indoles of claim 1 [3,2-b] carbazole derivative.
6. the method for manufacture of a kind of electroluminescent device as claimed in claim 5 is characterized in that may further comprise the steps: clean ito glass, nitrogen dries up, and reaches fully clean surface with ultraviolet ray-ozonize at last; According to the structure NPB that vapor deposition 40nm is thick on the ITO substrate successively in order of the device that is designed, the BCP that vapor deposition 10nm is thick; The boracic indoles of the said structure of claim 1 that vapor deposition 40nm is thick [3,2-b] carbazole derivative as the thick Bphen of luminescent layer, vapor deposition 40nm as the negative electrode of the thick aluminium of the thick lithium fluoride of electron transfer layer, vapor deposition 0.5nm and 150nm as device.
7. the method for manufacture of a kind of electroluminescent device as claimed in claim 6 is characterized in that described whole evaporate process all carries out under high vacuum, the evaporation rate of organic layer is controlled at 0.2-0.5nm/s, and the vapor deposition speed control of metal aluminium lamination is built in 0.5-1nm/s.
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| 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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