CN103897688A - Organic electroluminescent material and preparation method thereof, and organic electroluminescent device - Google Patents
Organic electroluminescent material and preparation method thereof, and organic electroluminescent device Download PDFInfo
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Abstract
The invention relates to an organic electroluminescent material and a preparation method and application thereof. The organic electroluminescent material has a structural formula as described in the specification. The structure of the organic electroluminescent material comprises a carbazole-thiophene structure with a hole transport characteristic and a 1,3,5-triazole structure with an electron transport characteristic, so the material has bipolar transport performance, which is favorable for charge balance of carriers in a recombination region and for obtainment of high luminous efficiency; meanwhile, a rigid 9-phenyl-substituted-carbazole structure enables the material to have heat stability. The organic electroluminescent material further has excellent dissolving performance and film forming performance and can be dissolved in frequently-used organic solvents like tetrahydrofuran, dichloromethane, trichloromethane and toluene.
Description
Technical field
The present invention relates to field of light emitting materials, relate in particular to a kind of electroluminescent organic material.The invention still further relates to preparation method and its application in organic electroluminescence device of this electroluminescent organic material.
Background technology
Along with the development of information age, there is the organic EL display (OLEDs) of efficient, energy-conservation, lightweight and big area white-light illuminating and be more and more subject to people's concern.As a kind of novel LED technology, Organic Light Emitting Diode (Organic Ligh Emitting Diode, OLED) technology is paid close attention to by global scientist, and relevant enterprise and laboratory are all in the research and development of carrying out this technology.Because of have active illuminating, light, thin, good contrast, energy consumption low, can be made into the features such as flexible device, so organic electroluminescence device has proposed higher requirement to preparing material.
1987, Eastman Kodak company of the U.S. reported the breakthrough in organic electroluminescent research.And to realize the application purposes such as panchromatic demonstration and illumination, luminescent device must have certain efficiency and life-span.Electroluminescent phosphorescence can be realized 100% electroluminescent efficiency in theory at present, and these are high more a lot of than fluorescence radiation (25% top efficiency in theory), but in current electroluminescent phosphorescence, the material of main part of the phosphorescence of high-quality also relatively lacks.
Summary of the invention
The object of the invention is to solve the problem and shortage that above-mentioned prior art exists, a kind of electroluminescent organic material and preparation method thereof is provided, also relate in addition the application of this electroluminescent organic material in organic electroluminescence device.In the structure of this electroluminescent organic material, have hole transport ability carbazole, thiophene-structure and electron-transporting 1,3,5-triazole structure, this makes material have bipolarity transmission performance, and the 9-phenyl substituted carbazole structure of rigidity makes material have certain thermostability simultaneously.
Electroluminescent organic material of the present invention has following structural formula:
The preparation method of above-mentioned machine semiconductor material comprises the following steps:
B) provide following compd A and B;
Compd A is
Compd B is
B) under atmosphere of inert gases, described compd A and described compd B are added according to the mol ratio of 1:1 ~ 2 in the organic solvent that contains catalyzer and basic solution, at 75～120 DEG C, carry out Suzuki coupling reaction 24～48 hours, separating-purifying, obtains the electroluminescent organic material of following structural formula:
Described catalyzer is organic palladium, and the mol ratio of described organic palladium and described compd A is 0.001 ~ 0.1:1.
Described organic palladium is tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride or three (dibenzalacetone) two palladiums.
Described rare gas element is nitrogen or argon gas.
Described basic solution is Cs
2cO
3, K
2cO
3or Na
2cO
3solution, the concentration of described basic solution is 2mol/L, the mol ratio of described basic solution and described compd A is 20 ~ 25:1.
Described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
Described separating-purifying step is as follows: the reaction solution that Suzuki coupling reaction is obtained is poured in saturated aqueous ammonium chloride, extract with methylene dichloride, the organic phase extracting is washed, is dried with sodium chloride aqueous solution, revolve steaming and obtain crude product except after desolventizing, more described crude product is carried out to silica gel column chromatography separating-purifying.
The invention also discloses the application of this electroluminescent organic material in organic electroluminescence devices, organic electroluminescence devices comprises anode, functional layer, luminescent layer and negative electrode, and the material of described luminescent layer is electroluminescent organic material of the present invention.
Compared with prior art, in the structure of electroluminescent organic material of the present invention, have hole transport ability carbazole, thiophene-structure and electron-transporting 1,3,5-triazole structure, this makes material have bipolarity transmission performance, be conducive to the charge balance of current carrier at recombination region, obtain high luminous efficiency, the 9-phenyl substituted carbazole structure of rigidity makes material have certain thermostability simultaneously.This electroluminescent organic material also has excellent solubility property and film forming properties, can be dissolved in common organic solvent as conventional in tetrahydrofuran (THF), methylene dichloride, trichloromethane, toluene etc.
Brief description of the drawings
Fig. 1 is the structure iron of the organic electroluminescence device prepared of embodiment 5.
Fig. 2 is the spectrogram of the organic electroluminescence device prepared of embodiment 5.
Embodiment
Below in conjunction with embodiment, the present invention is given to elaboration further.
Electroluminescent organic material of the present invention (being called for short P) has following structural formula, respectively called after TT2pC, TT2mC, T2TpC, T2TmC:
The present invention also comprises the preparation method of above-mentioned electroluminescent organic material, comprises the following steps:
A) get following compd A and B:
Wherein, compd A is
Compd B is
In compd B structural formula ,-B (OH)
2between can be on phenyl ring position or para-orientation, specifically can be expressed as following structural formula, wherein B1 be between position replace, B2 is para-orientation; Therefore,, under same process condition, compd A and compd B reaction, may obtain above-mentioned 4 kinds of electroluminescent organic materials, be called for short P, i.e. any in TT2pC, TT2mC, T2TpC, T2TmC.
B) under atmosphere of inert gases, described compd A and described compd B are added according to the mol ratio of 1:1 ~ 2 in the organic solvent that contains catalyzer and basic solution, at 75～120 DEG C, carry out Suzuki coupling reaction 24～48 hours, separating-purifying, obtains the electroluminescent organic material of following structural formula:
In described preparation method, the reaction formula of coupling reaction is as follows:
Catalyzer is organic palladium, and the mol ratio of organic palladium and compd A is 0.001 ~ 0.1:1, and organic palladium can be tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride or three (dibenzalacetone) two palladiums.
Rare gas element is nitrogen or argon gas, and basic solution is Cs
2cO
3, K
2cO
3or Na
2cO
3solution, the concentration of basic solution is 2mol/L, the mol ratio of basic solution and compd A is 20 ~ 25:1.Organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
In addition, the concrete steps of the purification by liquid extraction of above-mentioned steps in b) are as follows: the reaction solution that Suzuki coupling reaction is obtained is poured in saturated aqueous ammonium chloride, extract with methylene dichloride, the organic phase extracting is washed, is dried with sodium chloride aqueous solution, revolve steaming and obtain crude product except after desolventizing, more described crude product is carried out to silica gel column chromatography separating-purifying.
The present invention also comprises the electroluminescent organic material that utilizes above-mentioned preparation method to make, and this electroluminescent organic material can be applicable in organic electroluminescence device.Organic electroluminescence device generally comprises anode, functional layer, luminescent layer and negative electrode, and electroluminescent organic material of the present invention can be applicable in luminescent layer wherein.
Below in conjunction with accompanying drawing, preferred embodiment of the present invention is further described:
Embodiment 1
In the present embodiment, disclosed electroluminescent organic material is P1:9-(4-(4-(4-(9H-carbazole-9-yl) phenyl)-6-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole), called after TT2pC in the present invention, its structural formula is as follows:
For preparing this electroluminescent organic material, related method comprises the steps:
(1) get respectively compd A 1(2-that following structural formula represents chloro-4,6-bis-(thiophene-2-yl)-1,3,5-triazole) and compd B (4-(9H-carbazole-9-yl) phenyl-boron dihydroxide);
(2) by 4.0mmol compd A 1(2-chloro-4, 6-bis-(thiophene-2-yl)-1, 3, 5-triazole), 4.0mmol compd B (4-(9H-carbazole-9-yl) phenyl-boron dihydroxide) and 0.004mmol catalyzer (tetrakis triphenylphosphine palladium) join in reaction flask, vacuumize and logical nitrogen circulation 3 times after, make reaction system in anaerobic state, under nitrogen protection, add the Na of 65mL tetrahydrofuran solution, 2mol/L
2cO
3aqueous solution 40ml, mixed solution heating is carried out to Suzuki coupling reaction, at 75 ~ 80 DEG C of back flow reaction 48h, make and contain electroluminescent organic material 9-(4-(4-(4-(9H-carbazole-9-yl) phenyl)-6-(thiophene-2-yl)-1, 3, 5-triazole-2-yl) phenyl) reaction solution of-9H-carbazole, reaction solution is poured in the aqueous solution of saturated ammonium chloride, with dichloromethane extraction three times, the organic phase part sodium chloride aqueous solution extracting is washed, dry, revolve to steam except after desolventizing and obtain crude product, through silica gel column chromatography separating-purifying, finally obtain solid product 9-(4-(4-(4-(9H-carbazole-9-yl) the phenyl)-6-(thiophene-2-yl)-1 after purifying, 3, 5-triazole-2-yl) phenyl)-9H-carbazole.
The productive rate of 9-in the present embodiment (4-(4-(4-(9H-carbazole-9-yl) phenyl)-6-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole is 76%.
Gained compound is carried out to mass spectroscopy, and the test result obtaining is: MS:m/z646 (M
+).
Embodiment 2
In the present embodiment, disclosed electroluminescent organic material is P2:9-(3-(4-(3-((9H-carbazole-9-yl) phenyl)-6-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole, called after TT2mC in the present invention, its structural formula is as follows:
For preparing this electroluminescent organic material, related method comprises the steps:
(1) the compd A 2(2-that provides respectively following structural formula to represent is chloro-4,6-bis-(thiophene-2-yl)-1,3,5-triazole) and compd B (3-(9H-carbazole-9-yl) phenyl-boron dihydroxide),
(2) by 5.0mmol compd A 1(2-chloro-4, 6-bis-(thiophene-2-yl)-1, 3, 5-triazole), 6.0mmol compd B (9-p-methylphenyl-9H-carbazole-3-ylboronic acid) and 0.15mmol catalyzer (three (dibenzalacetone) two palladiums) join in reaction flask, vacuumize again after logical nitrogen circulation 3 times, make reaction system in anaerobic state, under nitrogen protection, add the K of 70mL glycol dimethyl ether, 2mol/L
2cO
3aqueous solution 55ml, mixed solution heating is carried out to Suzuki coupling reaction, at 100 DEG C of back flow reaction 40h, make and contain electroluminescent organic material 9-(3-(4-(3-((9H-carbazole-9-yl) phenyl)-6-(thiophene-2-yl)-1, 3, 5-triazole-2-yl) phenyl) reaction solution of-9H-carbazole, described reaction solution is poured in the aqueous solution of saturated ammonium chloride, with after dichloromethane extraction three times, the organic phase part sodium chloride aqueous solution extracting is washed, dry, revolve to steam except after desolventizing and obtain crude product, through silica gel column chromatography separating-purifying, finally obtain solid product 9-(3-(4-(3-((9H-carbazole-9-yl) the phenyl)-6-(thiophene-2-yl)-1 after purifying, 3, 5-triazole-2-yl) phenyl)-9H-carbazole.
(productive rate of 3-(4-(3-((9H-carbazole-9-yl) phenyl)-6-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole is 70% to 9-in the present embodiment.
Gained compound is carried out to mass spectroscopy, and the test result obtaining is: MS:m/z646 (M
+).
In the present embodiment, disclosed electroluminescent organic material is P3:9-(4-(4,6-bis-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole, called after T2TpC in the present invention, and its structural formula is as follows:
For preparing this electroluminescent organic material, related method comprises the steps:
Get respectively the compd A 2(2 that following structural formula represents, the chloro-6-of 4-bis-(thiophene-2-yl)-1,3,5-triazole) and compd B (4-(9H-carbazole-9-yl) phenyl-boron dihydroxide)
(2) by 5.0mmol compd A 2(2, the chloro-6-of 4-bis-(thiophene-2-yl)-1, 3, 5-triazole), 10.0mmol compd B (4-(9H-carbazole-9-yl) phenyl-boron dihydroxide) and 0.5mmol catalyzer (two (triphenylphosphine) palladium chloride) join in reaction flask, vacuumize again after logical nitrogen circulation 3 times, make reaction system in anaerobic state, under nitrogen protection, add the Cs of 60mL toluene solution, 2mol/L
2cO
3aqueous solution 58ml, mixed solution heating is carried out to Suzuki coupling reaction, at 120 DEG C of back flow reaction 24h, make and contain electroluminescent organic material 9-(4-(4, 6-bis-(thiophene-2-yl)-1, 3, 5-triazole-2-yl) phenyl) reaction solution of-9H-carbazole, reaction solution is poured in the aqueous solution of saturated ammonium chloride, with dichloromethane extraction three times, the organic phase part sodium chloride aqueous solution extracting is washed, dry, revolve to steam except after desolventizing and obtain crude product, through silica gel column chromatography separating-purifying, finally obtain the solid product 9-(4-(4 after purifying, 6-bis-(thiophene-2-yl)-1, 3, 5-triazole-2-yl) phenyl)-9H-carbazole.
The productive rate of 9-in the present embodiment (4-(4,6-bis-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole is 81%.
Gained compound is carried out to mass spectroscopy, and the test result obtaining is: MS:m/z487 (M
+).
Embodiment 4
In the present embodiment, disclosed electroluminescent organic material is P4:9-(3-(4,6-bis-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole, called after T2TmC in the present invention, and its structural formula is as follows:
For preparing this electroluminescent organic material, related method comprises the steps:
(1) the compd A 2(2 that provides respectively following structural formula to represent, the chloro-6-of 4-bis-(thiophene-2-yl)-1,3,5-triazole) and compd B (3-(9H-carbazole-9-yl) phenyl-boron dihydroxide);
(2) by 4.0mmol compd A 2(2, the chloro-6-of 4-bis-(thiophene-2-yl)-1, 3, 5-triazole), 10.0mmol compd B (3-(9H-carbazole-9-yl) phenyl-boron dihydroxide) and 0.07mmol catalyzer (tetrakis triphenylphosphine palladium) join in reaction flask, vacuumize again after logical nitrogen circulation 3 times, make reaction system in anaerobic state, under nitrogen protection, add 60mL tetrahydrofuran solution, the Na2CO3 aqueous solution 50ml of 2mol/L, mixed solution heating is carried out to Suzuki coupling reaction, at 80 DEG C of back flow reaction 48h, make and contain electroluminescent organic material 9-(3-(4, 6-bis-(thiophene-2-yl)-1, 3, 5-triazole-2-yl) phenyl) reaction solution of-9H-carbazole, reaction solution is poured in the aqueous solution of saturated ammonium chloride, with dichloromethane extraction three times, the organic phase part sodium chloride aqueous solution extracting is washed, dry, revolve to steam except after desolventizing and obtain crude product, through silica gel column chromatography separating-purifying, finally obtain the solid product 9-(3-(4 after purifying, 6-bis-(thiophene-2-yl)-1, 3, 5-triazole-2-yl) phenyl)-9H-carbazole.
The productive rate of 9-in the present embodiment (3-(4,6-bis-(thiophene-2-yl)-1,3,5-triazole-2-yl) phenyl)-9H-carbazole is 75%.
Gained compound is carried out to mass spectroscopy, and the test result obtaining is: MS:m/z487 (M
+).
Hole mobility and electronic mobility test
Hole mobility and electronic mobility that the electroluminescent organic material below above-described embodiment 1 ~ 4 being made records by time of flight method (Time of Flight, TOF).
As shown in table 1 test result, be 7.0 × 10 at electric field
5vcm
-1time, the hole mobility of the electroluminescent organic material that embodiment 1 ~ 4 makes is 1.0 × 10
-5cm
2(Vs)
-1above; Be 8.0 × 10 at electric field
5vcm
-1time, the electronic mobility of the electroluminescent organic material that embodiment 1 ~ 4 makes is also 1.0 × 10
-5cm
2(Vs)
-1above, illustrate that the present invention has good bipolarity transmission performance containing the electroluminescent organic material of carbazole.
Table 1
| Compound | Embodiment 1 | Embodiment 2 | |
Embodiment 4 |
| Hole mobility/cm 2(Vs) -1 | 7.1×10 -5 | 2.1×10 -5 | 9.7×10 -5 | 3.4×10 -5 |
| Electronic mobility/cm 2(Vs) -1 | 4.2×10 -5 | 1.4×10 -5 | 3.5×10 -5 | 1.1×10 -5 |
In the structure of electroluminescent organic material of the present invention, have hole transport ability carbazole, thiophene-structure and electron-transporting 1,3,5-triazole structure, this makes material have bipolarity transmission performance, be conducive to the charge balance of current carrier at recombination region, obtain high luminous efficiency, the 9-phenyl substituted carbazole structure of rigidity makes material have certain thermostability simultaneously.This electroluminescent organic material also has excellent solubility property and film forming properties, can be dissolved in common organic solvent as conventional in tetrahydrofuran (THF), methylene dichloride, trichloromethane, toluene etc.
Embodiment 5
The present embodiment is organic electroluminescence device, the electroluminescent organic material (P4) that the material of main part of its luminescent layer adopts embodiment 4 to make.
This organic electroluminescence device comprises the substrate, anode layer, hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer, cathode buffer layer and the cathode layer that stack gradually.Wherein:
Substrate adopts glass (Glass), and the material of anode layer is ITO, and ITO is prepared at glass surface, is called for short ito glass together with glass.Certainly, the material of anode layer can be also FTO, AZO, IZO.
The material of hole transmission layer is N, N '-bis-(Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines (NPB), thickness 40nm;
The material of luminescent layer is that three (2-phenylpyridines) close iridium (Ir (ppy)
3) be doped to composition doping mixing material in electroluminescent organic material (P4) according to the mass percent of 10wt%, be expressed as P4:Ir (ppy)
3, thickness 30nm;
The material of hole blocking layer is 2,9-dimethyl-4,7-phenylbenzene-9,10-phenanthroline (BCP), thickness 5nm;
The material of electron transfer layer is oxine aluminium (Alq
3), thickness 15nm;
The material of cathode buffer layer is that LiF is buffer layer, thickness 1nm;
The material of cathode layer is Al layer, thickness 120nm.
Therefore, as shown in Figure 1, the structure of this organic electroluminescence device is: glass/ITO/NPB/P4:
Ir(ppy)
3/BCP/Alq
3/LiF/Al。
The preparation technology of this organic electroluminescence device is as follows:
Stack gradually vacuum evaporation hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer, cathode buffer layer and cathode layer at the ITO of ito glass layer; After complete, make organic electroluminescence device.
This organic electroluminescence device is tested through at room temperature, in atmospheric environment, has obtained the maximum light efficiency of 26lm/W.
Fig. 2 is the spectrogram of the organic electroluminescence device prepared of embodiment 5.As can see from Figure 2, its maximum emission wavelength is at 510nm place, with Ir (ppy)
3intrinsic emission peak consistent.
Foregoing; it is only preferred embodiment of the present invention; not for limiting embodiment of the present invention; those of ordinary skill in the art are according to main design of the present invention and spirit; can carry out very easily corresponding flexible or amendment, therefore protection scope of the present invention should be as the criterion with the desired protection domain of claims.
Claims (9)
1. there is the electroluminescent organic material of following structural formula:
2. the preparation method of machine semiconductor material described in claim 1, the method comprises the following steps:
A) provide following compd A and B;
Compd A is
Compd B is
B) under atmosphere of inert gases, described compd A and described compd B are added according to the mol ratio of 1:1 ~ 2 in the organic solvent that contains catalyzer and basic solution, at 75～120 DEG C, carry out Suzuki coupling reaction 24～48 hours, separating-purifying, obtains the electroluminescent organic material of following structural formula:
3. preparation method according to claim 2, is characterized in that, described catalyzer is organic palladium, and the mol ratio of described organic palladium and described compd A is 0.001 ~ 0.1:1.
4. preparation method according to claim 3, is characterized in that, described organic palladium is tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride or three (dibenzalacetone) two palladiums.
5. preparation method according to claim 2, is characterized in that, described rare gas element is nitrogen or argon gas.
6. preparation method according to claim 2, is characterized in that, described basic solution is Cs
2cO
3, K
2cO
3or Na
2cO
3solution, the concentration of described basic solution is 2mol/L, the mol ratio of described basic solution and described compd A is 20 ~ 25:1.
7. preparation method according to claim 2, is characterized in that, described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
8. preparation method according to claim 2, it is characterized in that, described separating-purifying step is as follows: the reaction solution that Suzuki coupling reaction is obtained is poured in saturated aqueous ammonium chloride, extract with methylene dichloride, the organic phase extracting is washed, is dried with sodium chloride aqueous solution, revolve steaming and obtain crude product except after desolventizing, more described crude product is carried out to silica gel column chromatography separating-purifying.
9. an organic electroluminescence device, comprises anode, functional layer, luminescent layer and negative electrode, it is characterized in that, the material of described luminescent layer is electroluminescent organic material claimed in claim 1.
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| CN109836426A (en) * | 2017-11-28 | 2019-06-04 | 昆山国显光电有限公司 | The organic electroluminescence device of its preparation of 1,3,5- pyrrolotriazine derivatives and application |
| CN111675703A (en) * | 2020-05-22 | 2020-09-18 | 沅江华龙催化科技有限公司 | Method for constructing asymmetric 2,4, 6-trisubstituted 1,3,5-triazine compound by mixing aromatic aldehyde and ammonium iodide |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2017125572A1 (en) * | 2016-01-21 | 2017-07-27 | Ecole Polytechnique | Organic electroluminescent molecules |
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| CN111675703A (en) * | 2020-05-22 | 2020-09-18 | 沅江华龙催化科技有限公司 | Method for constructing asymmetric 2,4, 6-trisubstituted 1,3,5-triazine compound by mixing aromatic aldehyde and ammonium iodide |
| CN111675703B (en) * | 2020-05-22 | 2021-07-09 | 沅江华龙催化科技有限公司 | Method for constructing asymmetric 2,4, 6-trisubstituted 1,3,5-triazine compound by mixing aromatic aldehyde and ammonium iodide |
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Application publication date: 20140702 |