CN103288811A - Organic semiconductor material containing dibenzothiophene sulfone, preparation method of organic semiconductor material and organic electroluminescent device - Google Patents
Organic semiconductor material containing dibenzothiophene sulfone, preparation method of organic semiconductor material and organic electroluminescent device Download PDFInfo
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Abstract
The invention belongs to the field of organic electroluminescent materials and discloses an organic semiconductor material containing dibenzothiophene sulfone, a preparation method of the organic semiconductor material and an organic electroluminescent device. The organic semiconductor material has a general formula shown in a drawing, wherein R is a hydrogen atom or C1-C8 alkyl. The organic semiconductor material containing dibenzothiophene sulfone, disclosed by the invention, has excellent thermal stability and has good solubility and film forming property, and shown by spectrum tests, the maximum light emission wavelength of the material is located in a blue light range; meanwhile, due to the existence of carbazole and dibenzothiophene sulfone in the structure of the material, the material has bipolar transmission performance.
Description
Technical field
The present invention relates to electroluminescent organic material, relate in particular to a kind of dibenzothiophene sulfone organic semiconductor material and preparation method thereof that contains.The invention still further relates to a kind of use and contain dibenzothiophene sulfone organic semiconductor material as the organic electroluminescence device of luminescent layer.
Background technology
Along with the development of information age, have organic electroluminescent flat-panel monitor (OLEDs) and big area white-light illuminating efficient, energy-conservation, lightweight and more and more be subjected to people's attention.The OLED technology is paid close attention to by the scientist in the whole world, and relevant enterprise and laboratory are all in the research and development of carrying out this technology.As a kind of new LED technology, have active illuminating, light, thin, good contrast, energy consumption organic electroluminescence device low, that can be made into characteristics such as flexible device material has been proposed higher requirement.
1987, the Tang of U.S. Eastman Kodak company and VanSlyke reported the breakthrough in the organic electroluminescent research.And to realize application purposes such as panchromatic demonstration and illumination, luminescent device must have certain efficient and life-span.Efficient, stable at present blue light electroluminescence, white light parts are fewer, and the blue light material of high mobility, high thermal stability also relatively lacks.
Carbazole is the electron rich group, can improve the transmission performance of material, simultaneously because its plane rigid structure also helps the raising of material thermostability.And the dibenzothiophene sulfone is the electron deficiency group, can improve the electronic transmission performance of material, itself also is the rigid structure on a plane simultaneously, can improve the thermostability of material equally.
Summary of the invention
One of problem to be solved by this invention be to provide a kind of have good electronic transmission performance and a high thermal stability contain dibenzothiophene sulfone organic semiconductor material.
A kind of dibenzothiophene sulfone organic semiconductor material that contains has following chemical structure of general formula:
In the formula, R is hydrogen atom or C
1-C
8Alkyl; Preferred R is C
1-C
6Alkyl.
Two of problem to be solved by this invention is to provide the preparation method of above-mentioned electroluminescent organic material, and step is as follows:
Following compd A and compd B are provided:
Compd A is
Compd B is
(that is, 3-(carbazole-9-yl) phenylo boric acid, or 3-(3,6-alkyl carbazole-9-yl) phenylo boric acid) or
(that is, 3-(carbazole-9-yl) borate ester or 3-(3,6-alkyl carbazole-9-yl) borate ester), in the formula, R is hydrogen atom or C
1-C
8Alkyl; Preferably, R is C
1-C
6Alkyl
In atmosphere of inert gases, (be selected from the inert atmosphere that nitrogen or argon gas etc. constitute), 1: 2～1: 3 be dissolved in the organic solvent that contain catalyzer and alkali lye with mol ratio compd A and compd B, under 60～130 ℃, carry out Suzuki coupling reaction 20～40h, make structural formula and be
Contain dibenzothiophene sulfone organic semiconductor material (DRCzFSO); Reaction formula is as follows:
Among the above-mentioned preparation method, the mol ratio of preferred compound A and B is 1: 2.1.
State among the preparation method, compd A adopts following steps to make:
With structural formula be
The dibenzothiophene sulfone be dissolved in dense H
2SO
4In, at room temperature add NBS, make described compd A, wherein, every 30nmH
2SO
4The dibenzothiophene sulfone of middle dissolving 4mmol, the molar weight of NBS is 2.1 times of dibenzothiophene sulfone molar weight.
Among the above-mentioned preparation method, catalyzer is selected from tetrakis triphenylphosphine palladium, three (dibenzalacetone) two palladiums or two (triphenyl phosphorus) palladium chloride; The mole dosage of described catalyzer is 0.001～0.1 times of compd A mole dosage.
Among the above-mentioned preparation method, described alkali lye is Cs
2CO
3, K
2CO
3, Na
2CO
3Or Li
2CO
3In the solution any; In the described alkali lye, the consumption of alkali be compd A mole dosage 20-25 doubly.
Among the above-mentioned preparation method, preferred organic solvent is tetrahydrofuran (THF), glycol dimethyl ether, chlorobenzene or toluene.
Three of problem to be solved by this invention is providing a kind of organic electroluminescence device, and its luminescent layer material adopts the above-mentioned dibenzothiophene sulfone organic semiconductor material that contains.
The dibenzothiophene sulfone organic semiconductor material that contains provided by the invention characterizes the performance that this kind contains dibenzothiophene sulfone organic semiconductor material by differential thermal analysis, scanning, and the result shows that this material has excellent thermostability; Carbazole is the electron rich group, can improve the transmission performance of material, simultaneously because its plane rigid structure, also help the raising of material thermostability, and the dibenzothiophene sulfone is the electron deficiency group, can improve the electronic transmission performance of material, itself also be the rigid structure on a plane simultaneously, can improve the thermostability of material equally;
Such material has good solubility and film-forming properties, and by spectrum test, finds that the maximum emission wavelength of this material at blue light range, has wideer energy gap; This luminescent material makes material have the bipolarity transmission performance owing to the existence of carbazole in the structure and dibenzothiophene sulfone simultaneously.
The preparation method who contains dibenzothiophene sulfone organic semiconductor material provided by the invention, technology is simple, is easy to control.
Description of drawings
Fig. 1 is the organic electroluminescence device structural representation of embodiment 5;
Fig. 2 is the organic electroluminescence device luminescent spectrum figure of embodiment 5.
Embodiment
Below in conjunction with accompanying drawing, preferred embodiment of the present invention is described in further detail.
What present embodiment disclosed following structure contains dibenzothiophene sulfone organic semiconductor material, and namely 2,7-two (3-(carbazole-9-yl) phenyl) dibenzothiophene sulfone (DCzFSO):
4mmol dibenzothiophene sulfone is dissolved in the dense H of 30ml
2SO
4In, at room temperature add 8.2mmolNBS, stir.Behind the 24h, reaction solution is poured in the water into suction filtration, water and methanol wash.Remaining solid recrystallization in chlorobenzene obtains colourless needle-like solid 2,7-dibromo dibenzothiophene sulfone.Productive rate: 49%.MS：m/z?374(M
+)。
With 2; 7-dibromo dibenzothiophene sulfone 3mmol, 3-(carbazole-9-yl) phenylo boric acid 6.3mmol, 0.27mmol tetra-triphenylphosphine palladium join in the reactor; vacuumize, after the logical nitrogen circulation 3 times; reaction system is under the nitrogen protection, and adding 50mL anhydrous tetrahydrofuran solution, 30ml concentration are the Na of 2mol/L
2CO
3The aqueous solution is adjusted to 60 ℃ with temperature of reaction system, backflow Suzuki coupling reaction 40h.After reaction finishes, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, dry, obtain crude product after revolving the steaming desolventizing, separate to purify obtaining 2 of yellow, 7-two (3-(carbazole-9-yl) phenyl) dibenzothiophene sulfone solid product through silica gel column chromatography.Productive rate: 92%.MS：m/z700(M
+)。
What present embodiment disclosed following structure contains dibenzothiophene sulfone organic semiconductor material, and namely 2,7-two (3-(3,6-di-t-butyl carbazole-9-yl) phenyl) dibenzothiophene sulfone (Dt-BuCzFSO):
Step 1: identical with the step 1 of embodiment 1;
The preparation of step 2: 2,7-two (3-(3,6-di-t-butyl carbazole-9-yl) phenyl) dibenzothiophene sulfone (Dt-BuCzFSO):
With 2; 7-dibromo dibenzothiophene sulfone sulfone 3mmol, 3-(3; 6-di-t-butyl carbazole-9-yl) phenylo boric acid 9.0mmol, three (dibenzalacetone) two palladium 0.03mmol join in the reaction flask; vacuumize, after the logical nitrogen circulation 3 times; make reaction system be in anaerobic state; under the nitrogen protection, add the K of toluene solution 50mL, 2mol/L
2CO
3Aqueous solution 45ml is heated to 115 ℃ of backflow Suzuki coupling reaction 30h with mixed solution.After reaction finishes, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, dry, obtain crude product after revolving the steaming desolventizing, separate to purify obtaining 2 of yellow, 7-two (3-(carbazole-9-yl) phenyl) dibenzothiophene sulfone solid product through silica gel column chromatography.Productive rate: 89%.MS：m/z?924(M
+)。
What present embodiment disclosed following structure contains dibenzothiophene sulfone organic semiconductor material, and namely 2,7-two (3-(3,6-di-n-hexyl carbazole-9-yl) phenyl) dibenzothiophene sulfone (DHCzFSO):
Step 1: identical with the step 1 of embodiment 1;
The preparation of step 2: 2,7-two (3-(3,6-di-n-hexyl carbazole-9-yl) phenyl) dibenzothiophene sulfone (DHCzFSO):
With 2; 7-dibromo dibenzothiophene sulfone sulfone 3mmol, 3-(3; 6-di-n-hexyl carbazole-9-yl) borate ester 6.4mmol, two (triphenyl phosphorus) palladium chloride 0.003mmol join in the reaction flask; vacuumize, after the logical nitrogen circulation 3 times; make reaction system be in anaerobic state; under the nitrogen protection, add the Li of ethylene glycol dimethyl ether solution 55mL, 2mol/L
2CO
3Aqueous solution 45ml is heated to 100 ℃ of backflow Suzuki coupling reaction 20h with mixed solution.After reaction finishes, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, and drying is revolved and obtained crude product after steaming desolventizing, separate purification through silica gel column chromatography, obtain 2,7-two (3-(3,6-di-n-hexyl carbazole-9-yl) phenyl) dibenzothiophene sulfone solid product.Productive rate: 90%.MS：m/z?1036(M
+)。
What present embodiment disclosed following structure contains dibenzothiophene sulfone organic semiconductor material, and namely 2,7-two (3-(3,6-di-n-octyl carbazole-9-yl) phenyl) dibenzothiophene sulfone (DOCzFSO):
Step 1: identical with the step 1 of embodiment 1;
The preparation of step 2: 2,7-two (3-(3,6-di-n-octyl carbazole-9-yl) phenyl) dibenzothiophene sulfone (DOCzFSO):
With 2; 7-dibromo dibenzothiophene sulfone sulfone 3mmol, 3-(3; 6-di-n-octyl carbazole-9-yl) borate ester 6.0mmol, two (triphenyl phosphorus) palladium chloride 0.3mmol join in the reaction flask; vacuumize, after the logical argon gas circulation 3 times; make reaction system be in anaerobic state; under the argon shield, add the Cs of chlorobenzene solution 50mL, 2mol/L
2CO
3Aqueous solution 34ml is heated to 130 ℃ of backflow Suzuki coupling reaction 20h with mixed solution.After reaction finishes, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, drying is revolved and is obtained crude product after steaming desolventizing, separates through silica gel column chromatography and purifies, obtain 2,7-two (3-(carbazole-9-yl) phenyl) dibenzothiophene sulfone solid product.Productive rate: 93%.MS：m/z?1148(M
+)。
Present embodiment is organic electroluminescence device, its luminescent layer adopt that embodiment 1 makes 2,7-two (3-(carbazole-9-yl) phenyl) dibenzothiophene sulfone (DCzFSO).
The structure of this organic electroluminescence device as shown in Figure 1; Comprise the anode 1, the hole injection layer 2 on the anode 1 that stack gradually, be positioned at the electron injecting layer 6 on hole transmission layer 3, the luminescent layer 4 on the hole transmission layer 3, the hole blocking layer on the luminescent layer 4 or electron transfer layer 5, hole blocking layer or the electron transfer layer 5 on this hole injection layer 2, and be positioned at the negative electrode 7 on this electron injecting layer 6.
The material of anode 1 is ito glass, namely comprises glass 11 and the ITO film 12 that is positioned on this glass 11; The material of hole injection layer 2 is m-MTDATA (4,4 ', 4 " three (N-3-aminomethyl phenyl-N-phenyl amino) dibenzothiophene sulfone); the material of hole transmission layer 3 be NPB (N; N '-two (Alpha-Naphthyl)-N; N '-phenylbenzene-4; 4 '-diamines); the material of luminescent layer 4 is the DCzFSO{2 among the embodiment 1,7-two (3-(carbazole-9-yl) phenyl) dibenzothiophene sulfone } mix 11wt%FIrpic{ two (4 for material of main part, 6-difluorophenyl pyridine-N, C2 ') the pyridine formyl closes iridium } the blue phosphorescent material, the material of hole blocking layer or electron transfer layer 5 is TPBI (1,3,5-three (1-phenyl-1H-benzimidazolyl-2 radicals-yl) benzene), the material of electron injecting layer 6 is LiF, the material of negative electrode 7 be Mg: Ag (10: 1, wt%) alloy.This hole injection layer 2, hole transmission layer 3, luminescent layer 4, hole blocking layer or electron transfer layer 5, electron injecting layer 6 and negative electrode 7 make by the vacuum evaporation mode.
See also Fig. 2, Fig. 2 show should use-case the luminescent spectrum figure of electroluminescent device when voltage is 5.5V, from Fig. 2 can, its maximum emission wavelength is at 475nm.And test through at room temperature, under the atmospheric environment, the external quantum efficiency of this blue light OLED device is 17.7%.
Should be understood that above-mentioned statement at preferred embodiment of the present invention is comparatively detailed, can not therefore think the restriction to scope of patent protection of the present invention, scope of patent protection of the present invention should be as the criterion with claims.
Claims (9)
1. one kind contains dibenzothiophene sulfone organic semiconductor material, it is characterized in that, this contains dibenzothiophene sulfone organic semiconductor material and has following general formula:
In the formula, R is hydrogen atom or C
1-C
8Alkyl.
2. a preparation method who contains dibenzothiophene sulfone organic semiconductor material is characterized in that, this preparation method comprises the steps:
Following compd A and compd B are provided:
Compd A is
Compd B is
Or
In the formula, R is hydrogen atom or C
1-C
8Alkyl;
In atmosphere of inert gases, compd A and compd B were dissolved in the organic solvent that contains catalyzer and alkali lye with mol ratio in 1: 2～1: 3, under 60～130 ℃, carry out Suzuki coupling reaction 20～40h, make structural formula and be
Contain dibenzothiophene sulfone organic semiconductor material.
3. the preparation method who contains dibenzothiophene sulfone organic semiconductor material according to claim 2 is characterized in that described compd A is to adopt following steps to make:
With structural formula be
The dibenzothiophene sulfone be dissolved in dense H
2SO
4In, at room temperature add NBS, make described compd A, wherein, every 30nmH
2SO
4The dibenzothiophene sulfone of middle dissolving 4mmol, the molar weight of NBS is 2.1 times of dibenzothiophene sulfone molar weight.
4. the preparation method who contains dibenzothiophene sulfone organic semiconductor material according to claim 2 is characterized in that, described catalyzer is selected from tetrakis triphenylphosphine palladium, three (dibenzalacetone) two palladiums or two (triphenyl phosphorus) palladium chloride.
5. according to claim 2 or the 4 described preparation methods that contain dibenzothiophene sulfone organic semiconductor material, it is characterized in that the mole dosage of described catalyzer is 0.001～0.1 times of compd A mole dosage.
6. the preparation method who contains dibenzothiophene sulfone organic semiconductor material according to claim 2 is characterized in that, described alkali lye is Cs
2CO
3, K
2CO
3, Na
2CO
3Or Li
2CO
3Solution.
7. according to claim 2 or the 7 described preparation methods that contain dibenzothiophene sulfone organic semiconductor material, it is characterized in that, in the described alkali lye, the consumption of alkali be compd A mole dosage 20-25 doubly.
8. the preparation method who contains dibenzothiophene sulfone organic semiconductor material according to claim 2 is characterized in that, described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether, chlorobenzene or toluene.
9. an organic electroluminescence device is characterized in that, its luminescent layer material adopts claim 1 or the 2 described dibenzothiophene sulfone organic semiconductor material that contain.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103694992A (en) * | 2013-12-26 | 2014-04-02 | 深圳市华星光电技术有限公司 | Thermal activation delay fluorescent material and synthesis method thereof as well as OLED device using thermal activation delay fluorescent material |
| CN103833727A (en) * | 2014-02-24 | 2014-06-04 | 华南理工大学 | Soluble dendron substituted S,S-dioxo-dibenzothiophene based blue-light molecular glass material as well as preparation method and application thereof |
| CN107129486A (en) * | 2017-05-22 | 2017-09-05 | 华南理工大学 | Bipolarity blue light small molecule emitter material and its preparation method and application based on naphtho- 8 S, S dioxydibenze bithiophene unit |
| CN107129485A (en) * | 2017-05-18 | 2017-09-05 | 华南理工大学 | Bipolarity small molecule emitter material and its preparation method and application based on naphtho- 2,7 S, S dioxydibenze bithiophene unit |
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Cited By (7)
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|---|---|---|---|---|
| CN103694992A (en) * | 2013-12-26 | 2014-04-02 | 深圳市华星光电技术有限公司 | Thermal activation delay fluorescent material and synthesis method thereof as well as OLED device using thermal activation delay fluorescent material |
| CN103833727A (en) * | 2014-02-24 | 2014-06-04 | 华南理工大学 | Soluble dendron substituted S,S-dioxo-dibenzothiophene based blue-light molecular glass material as well as preparation method and application thereof |
| CN103833727B (en) * | 2014-02-24 | 2016-03-02 | 华南理工大学 | The S that soluble branch replaces, S-dioxo-dibenzothiophene base blue light molecular glass material and preparation method thereof and application |
| CN107129485A (en) * | 2017-05-18 | 2017-09-05 | 华南理工大学 | Bipolarity small molecule emitter material and its preparation method and application based on naphtho- 2,7 S, S dioxydibenze bithiophene unit |
| CN107129485B (en) * | 2017-05-18 | 2020-12-22 | 华南理工大学 | Bipolar small-molecule luminescent material based on naphtho-2, 7-S, S-dioxo dibenzothiophene unit and preparation method and application thereof |
| CN107129486A (en) * | 2017-05-22 | 2017-09-05 | 华南理工大学 | Bipolarity blue light small molecule emitter material and its preparation method and application based on naphtho- 8 S, S dioxydibenze bithiophene unit |
| CN107129486B (en) * | 2017-05-22 | 2020-11-24 | 华南理工大学 | Bipolar blue light small molecule luminescent material based on naphtho-8-S, S-dioxo dibenzothiophene unit and preparation method and application thereof |
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