CN103288811B - Containing dibenzothiophene sulphone organic semiconductor material, its preparation method and organic electroluminescence device - Google Patents
Containing dibenzothiophene sulphone organic semiconductor material, its preparation method and organic electroluminescence device Download PDFInfo
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- CN103288811B CN103288811B CN201210045917.4A CN201210045917A CN103288811B CN 103288811 B CN103288811 B CN 103288811B CN 201210045917 A CN201210045917 A CN 201210045917A CN 103288811 B CN103288811 B CN 103288811B
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- dibenzothiophene sulphone
- semiconductor material
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- 0 *=S1(c2cc(Br)ccc2-c(cc2)c1cc2Br)=O Chemical compound *=S1(c2cc(Br)ccc2-c(cc2)c1cc2Br)=O 0.000 description 2
- CDZXSXVEOHSBGJ-UHFFFAOYSA-N CCCCCCCCc(cc1)cc(c2cc(C)ccc22)c1[n]2-c1cc(-c2ccc(-c(c(S3(=N)=O)c4)ccc4-c4cc(-[n]5c(ccc(CCCCCCCC)c6)c6c6cc(CCCCCCCC)ccc56)ccc4)c3c2)ccc1 Chemical compound CCCCCCCCc(cc1)cc(c2cc(C)ccc22)c1[n]2-c1cc(-c2ccc(-c(c(S3(=N)=O)c4)ccc4-c4cc(-[n]5c(ccc(CCCCCCCC)c6)c6c6cc(CCCCCCCC)ccc56)ccc4)c3c2)ccc1 CDZXSXVEOHSBGJ-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention belongs to field of organic electroluminescent materials, it discloses a kind of containing dibenzothiophene sulphone organic semiconductor material, its preparation method and organic electroluminescence device; Following general formula should be had containing dibenzothiophene sulphone organic semiconductor material:
in formula, R is hydrogen atom or C
1-C
8alkyl.Provided by the invention containing dibenzothiophene sulphone organic semiconductor material, there is excellent thermostability, there is good solubility and film-forming properties, and by spectrum test, find that the maximum emission wavelength of this material is at blue light range; Simultaneously this luminescent material is due to the existence of carbazole in structure and dibenzothiophene sulphone, makes material have bipolar transmission performance.
Description
Technical field
The present invention relates to electroluminescent organic material, particularly relate to a kind of containing dibenzothiophene sulphone organic semiconductor material and preparation method thereof.The invention still further relates to a kind of use containing the organic electroluminescence device of dibenzothiophene sulphone organic semiconductor material as luminescent layer.
Background technology
Along with the development of information age, there is the concern that the organic EL display (OLEDs) of efficient, energy-conservation, lightweight and big area white-light illuminating are more and more subject to people.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 carrying out this technology.As a kind of novel LED technology, there is active illuminating, light, thin, good contrast, energy consumption are low, organic electroluminescence device that is that can be made into the features such as flexible device proposes higher requirement to material.
1987, Tang and VanSlyke of EastmanKodak company of the U.S. reported the breakthrough in organic electroluminescent research.And the application purpose such as total colouring and illumination will be realized, luminescent device must have certain efficiency and life-span.Blue light electroluminescence efficient, stable at present, white light parts are fewer, and the blue light material of high mobility, high thermal stability also compares shortage.
Carbazole is electron rich group, can improve the transmission performance of material, simultaneously due to its plane rigid structure, also contributes to the raising of material thermostability.And dibenzothiophene sulphone is electron deficiency group, the electronic transmission performance of material can be improved, itself also be the rigid structure of a plane simultaneously, the thermostability of material can be improved equally.
Summary of the invention
One of problem to be solved by this invention be to provide a kind of electronic transmission performance of having had and high thermal stability containing dibenzothiophene sulphone organic semiconductor material.
A kind of containing dibenzothiophene sulphone organic semiconductor material, there is following chemical structure of general formula:
In 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 the preparation method providing 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-base) phenylo boric acid, or 3-(3,6-alkyl carbazole-9-base) phenylo boric acid) or
(that is, 3-(carbazole-9-base) borate ester or 3-(3,6-alkyl carbazole-9-base) borate ester), in formula, R is hydrogen atom or C
1-C
8alkyl; Preferably, R is C
1-C
6alkyl
(inert atmosphere that nitrogen or argon gas etc. are formed is selected from) in atmosphere of inert gases, compd A and compd B are dissolved in the organic solvent containing catalyzer and alkali lye with mol ratio 1: 2 ~ 1: 3, at 60 ~ 130 DEG C, carry out Suzuki coupling reaction 20 ~ 40h, obtained structural formula is
containing dibenzothiophene sulphone organic semiconductor material (DRCzFSO); Reaction formula is as follows:
In above-mentioned preparation method, the mol ratio of preferred compound A and B is 1: 2.1.
State in preparation method, compd A adopts following steps to obtain:
By structural formula be
dibenzothiophene sulphone be dissolved in dense H
2sO
4in, at room temperature add NBS, obtained described compd A, wherein, every 30nmH
2sO
4the dibenzothiophene sulphone of middle dissolving 4mmol, the molar weight of NBS is 2.1 times of dibenzothiophene sulphone molar weight.
In above-mentioned preparation method, catalyzer is selected from tetrakis triphenylphosphine palladium, three (dibenzalacetone) two palladium or two (triphenyl phosphorus) palladium chloride; The mole dosage of described catalyzer is 0.001 ~ 0.1 times of compd A mole dosage.
In above-mentioned preparation method, described alkali lye is Cs
2cO
3, K
2cO
3, Na
2cO
3or Li
2cO
3any one in solution; In described alkali lye, the consumption of alkali is 20-25 times of the mole dosage of compd A.
In 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 emitting layer material adopts above-mentioned containing dibenzothiophene sulphone organic semiconductor material.
Provided by the invention containing dibenzothiophene sulphone organic semiconductor material, by differential thermal analysis, scan and characterize the performance of this kind containing dibenzothiophene sulphone organic semiconductor material, result shows that this material has excellent thermostability; Carbazole is electron rich group, the transmission performance of material can be improved, simultaneously due to its plane rigid structure, also the raising of material thermostability is contributed to, and dibenzothiophene sulphone is electron deficiency group, the electronic transmission performance of material can be improved, itself be also the rigid structure of a plane simultaneously, the thermostability of material can be improved equally;
Such material has good solubility and film-forming properties, and by spectrum test, finds that the maximum emission wavelength of this material is at blue light range, has wider energy gap; Simultaneously this luminescent material is due to the existence of carbazole in structure and dibenzothiophene sulphone, makes material have bipolar transmission performance.
Preparation method containing dibenzothiophene sulphone organic semiconductor material provided by the invention, technique is simple, is easy to control.
Accompanying drawing explanation
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.
Embodiment 1
The present embodiment openly following structure containing dibenzothiophene sulphone organic semiconductor material, i.e. 2,7-bis-(3-(carbazole-9-base) phenyl) dibenzothiophene sulphone (DCzFSO):
The preparation of step one, 2,7-dibromo dibenzothiophene sulphone:
4mmol dibenzothiophene sulphone is dissolved in the dense H of 30ml
2sO
4in, at room temperature add 8.2mmolNBS, stir.After 24h, reaction solution is poured into water, suction filtration, by water and methanol wash.Remaining solid recrystallization in chlorobenzene, obtains colourless needles solid 2,7-dibromo dibenzothiophene sulphone.Productive rate: 49%.MS：m/z374(M
+)。
The preparation of step 2,2,7-bis-(3-(carbazole-9-base) phenyl) dibenzothiophene sulphone (DCzFSO):
By 2; 7-dibromo dibenzothiophene sulphone 3mmol, 3-(carbazole-9-base) phenylo boric acid 6.3mmol, 0.27mmol tetra-triphenylphosphine palladium joins in reactor; vacuumize, after logical nitrogen circulation 3 times; under making reaction system be in nitrogen protection, add 50mL anhydrous tetrahydrofuran solution, 30ml concentration is the Na of 2mol/L
2cO
3the aqueous solution, adjusts to 60 DEG C by temperature of reaction system, backflow Suzuki coupling reaction 40h.After reaction terminates, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase sodium chloride aqueous solution is washed, dry, revolve to steam and obtain crude product except after desolventizing, obtain yellow 2,7-bis-(3-(carbazole-9-base) phenyl) dibenzothiophene sulphone solid product through silica gel column chromatography separating-purifying.Productive rate: 92%.MS：m/z700(M
+)。
Embodiment 2
The present embodiment openly following structure containing dibenzothiophene sulphone organic semiconductor material, i.e. 2,7-bis-(3-(3,6-di-t-butyl carbazole-9-base) phenyl) dibenzothiophene sulphone (Dt-BuCzFSO):
Step one: identical with the step one of embodiment 1;
The preparation of step 2: 2,7-bis-(3-(3,6-di-t-butyl carbazole-9-base) phenyl) dibenzothiophene sulphone (Dt-BuCzFSO):
By 2; 7-dibromo dibenzothiophene sulphone sulfone 3mmol, 3-(3; 6-di-t-butyl carbazole-9-base) phenylo boric acid 9.0mmol, three (dibenzalacetone) two palladium 0.03mmol join in reaction flask; vacuumize, after logical nitrogen circulation 3 times; reaction system is made to be in anaerobic state; under nitrogen protection, add the K of toluene solution 50mL, 2mol/L
2cO
3aqueous solution 45ml, is heated to 115 DEG C of backflow Suzuki coupling reaction 30h by mixed solution.After reaction terminates, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase sodium chloride aqueous solution is washed, dry, revolve to steam and obtain crude product except after desolventizing, obtain yellow 2,7-bis-(3-(carbazole-9-base) phenyl) dibenzothiophene sulphone solid product through silica gel column chromatography separating-purifying.Productive rate: 89%.MS：m/z924(M
+)。
Embodiment 3
The present embodiment openly following structure containing dibenzothiophene sulphone organic semiconductor material, i.e. 2,7-bis-(3-(3,6-di-n-hexyl carbazole-9-base) phenyl) dibenzothiophene sulphone (DHCzFSO):
Step one: identical with the step one of embodiment 1;
The preparation of step 2: 2,7-bis-(3-(3,6-di-n-hexyl carbazole-9-base) phenyl) dibenzothiophene sulphone (DHCzFSO):
By 2; 7-dibromo dibenzothiophene sulphone sulfone 3mmol, 3-(3; 6-di-n-hexyl carbazole-9-base) borate ester 6.4mmol, two (triphenyl phosphorus) palladium chloride 0.003mmol join in reaction flask; vacuumize, after logical nitrogen circulation 3 times; reaction system is made to be in anaerobic state; under nitrogen protection, add the Li of ethylene glycol dimethyl ether solution 55mL, 2mol/L
2cO
3aqueous solution 45ml, is heated to 100 DEG C of backflow Suzuki coupling reaction 20h by mixed solution.After reaction terminates, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase sodium chloride aqueous solution is washed, dry, revolves to steam to obtain crude product except after desolventizing, through silica gel column chromatography separating-purifying, obtain 2,7-bis-(3-(3,6-di-n-hexyl carbazole-9-base) phenyl) dibenzothiophene sulphone solid product.Productive rate: 90%.MS：m/z1036(M
+)。
Embodiment 4
The present embodiment openly following structure containing dibenzothiophene sulphone organic semiconductor material, i.e. 2,7-bis-(3-(3,6-di-n-octyl carbazole-9-base) phenyl) dibenzothiophene sulphone (DOCzFSO):
Step one: identical with the step one of embodiment 1;
The preparation of step 2: 2,7-bis-(3-(3,6-di-n-octyl carbazole-9-base) phenyl) dibenzothiophene sulphone (DOCzFSO):
By 2; 7-dibromo dibenzothiophene sulphone sulfone 3mmol, 3-(3; 6-di-n-octyl carbazole-9-base) borate ester 6.0mmol, two (triphenyl phosphorus) palladium chloride 0.3mmol join in reaction flask; vacuumize, after logical argon cycles 3 times; reaction system is made to be in anaerobic state; under argon shield, add the Cs of chlorobenzene solution 50mL, 2mol/L
2cO
3aqueous solution 34ml, is heated to 130 DEG C of backflow Suzuki coupling reaction 20h by mixed solution.After reaction terminates, reaction solution is poured in the aqueous solution of saturated ammonium chloride, dichloromethane extraction three times, organic phase sodium chloride aqueous solution is washed, drying, revolves steaming and obtains crude product, through silica gel column chromatography separating-purifying except after desolventizing, obtain 2,7-bis-(3-(carbazole-9-base) phenyl) dibenzothiophene sulphone solid product.Productive rate: 93%.MS：m/z1148(M
+)。
Embodiment 5
The present embodiment is organic electroluminescence device, 2,7-bis-(3-(carbazole-9-base) phenyl) dibenzothiophene sulphone (DCzFSO) that its luminescent layer adopts embodiment 1 obtained.
The structure of this organic electroluminescence device as shown in Figure 1; Comprise stack gradually anode 1, hole injection layer 2 on anode 1, be positioned at the hole blocking layer on the hole transmission layer 3 on this hole injection layer 2, the luminescent layer 4 on hole transmission layer 3, luminescent layer 4 or the electron injecting layer 6 on electron transfer layer 5, hole blocking layer or electron transfer layer 5, and be positioned at the negative electrode 7 on this electron injecting layer 6.
The material of anode 1 is ito glass, the ito film 12 namely comprising glass 11 and be positioned on this glass 11, the material of hole injection layer 2 is m-MTDATA (4, 4 ', 4 "-three (N-3-methylphenyl-N-phenyl is amino) dibenzothiophene sulphone), the material of hole transmission layer 3 is NPB (N, N '-two (Alpha-Naphthyl)-N, N '-phenylbenzene-4, 4 '-diamines), the material of luminescent layer 4 is the DCzFSO{2 in embodiment 1, 7-bis-(3-(carbazole-9-base) phenyl) dibenzothiophene sulphone } mix 11wt%FIrpic{ two (4 for material of main part, 6-difluorophenyl pyridinato-N, C2 ') pyridinecarboxylic conjunction iridium } blue phosphor materials, the material of hole blocking layer or electron transfer layer 5 is TPBI (1, 3, 5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene), the material of electron injecting layer 6 is LiF, the material of negative electrode 7 is 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 are obtained by vacuum evaporation mode.
Refer to Fig. 2, Fig. 2 display should the luminescent spectrum figure of electroluminescent device when voltage is 5.5V of use-case, and passable from Fig. 2, its maximum emission wavelength is at 475nm.And test through at room temperature, under atmospheric environment, the external quantum efficiency of this Nan dian Yao device is 17.7%.
Should be understood that, the above-mentioned statement for present pre-ferred embodiments is comparatively detailed, and therefore can not 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 (7)
1. containing a dibenzothiophene sulphone organic semiconductor material, it is characterized in that should having following general formula containing dibenzothiophene sulphone organic semiconductor material:
In formula, R is hydrogen atom or C
1-C
8alkyl.
2., containing a preparation method for dibenzothiophene sulphone organic semiconductor material, it 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 formula, R is hydrogen atom or C
1-C
8alkyl;
In atmosphere of inert gases, compd A and compd B be dissolved in the organic solvent containing catalyzer and alkali lye with mol ratio 1:2 ~ 1:3, at 60 ~ 130 DEG C, carry out Suzuki coupling reaction 20 ~ 40h, obtained structural formula is
containing dibenzothiophene sulphone organic semiconductor material;
In described alkali lye, the consumption of alkali is 20 ~ 25 times of the mole dosage of compd A;
The mole dosage of described catalyzer is 0.001 ~ 0.1 times of compd A mole dosage.
3. the preparation method containing dibenzothiophene sulphone organic semiconductor material according to claim 2, is characterized in that described compd A adopts following steps to obtain:
By structural formula be
dibenzothiophene sulphone be dissolved in dense H
2sO
4in, at room temperature add NBS, obtained described compd A, wherein, every 30nmH
2sO
4the dibenzothiophene sulphone of middle dissolving 4mmol, the molar weight of NBS is 2.1 times of dibenzothiophene sulphone molar weight.
4. the preparation method containing dibenzothiophene sulphone organic semiconductor material according to claim 2, it is characterized in that, described catalyzer is selected from tetrakis triphenylphosphine palladium, three (dibenzalacetone) two palladium or two (triphenyl phosphorus) palladium chloride.
5. the preparation method containing dibenzothiophene sulphone organic semiconductor material according to claim 2, it is characterized in that, described alkali lye is Cs
2cO
3, K
2cO
3, Na
2cO
3or Li
2cO
3solution.
6. the preparation method containing dibenzothiophene sulphone organic semiconductor material according to claim 2, it is characterized in that, described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether, chlorobenzene or toluene.
7. an organic electroluminescence device, is characterized in that, its emitting layer material adopts according to claim 1 containing dibenzothiophene sulphone organic semiconductor material.
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| CN103694992B (en) * | 2013-12-26 | 2016-03-16 | 深圳市华星光电技术有限公司 | Hot activation delayed fluorescence material, its synthetic method and use the OLED of this hot activation delayed fluorescence material |
| 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 |
| 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 |
| 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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| CN1470501A (en) * | 2002-06-27 | 2004-01-28 | 因芬尼昂技术股份公司 | Insulated material monomer in aluminium and copper technology |
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