CN103172651A - Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device - Google Patents
Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device Download PDFInfo
- Publication number
- CN103172651A CN103172651A CN2011104358267A CN201110435826A CN103172651A CN 103172651 A CN103172651 A CN 103172651A CN 2011104358267 A CN2011104358267 A CN 2011104358267A CN 201110435826 A CN201110435826 A CN 201110435826A CN 103172651 A CN103172651 A CN 103172651A
- Authority
- CN
- China
- Prior art keywords
- semiconductor material
- organic semiconductor
- dibenzothiophene sulfone
- solution
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 *c(cc1)cc2c1-c(ccc(Br)c1)c1S2(=O)=O Chemical compound *c(cc1)cc2c1-c(ccc(Br)c1)c1S2(=O)=O 0.000 description 3
- LUDZJVZEBHTEBB-UHFFFAOYSA-N O=S1(c2cc(Br)ccc2-c(cc2)c1cc2Br)=O Chemical compound O=S1(c2cc(Br)ccc2-c(cc2)c1cc2Br)=O LUDZJVZEBHTEBB-UHFFFAOYSA-N 0.000 description 1
Images
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to organic semiconductor materials, and discloses a dibenzothiophene sulphone containing organic semiconductor material and a preparation method thereof and an organic electroluminescent device. The dibenzothiophene sulphone containing organic semiconductor material has the chemical structural formula as shown in the specification, wherein A- is -F, -CN or -NO2. According to the dibenzothiophene sulphone containing organic semiconductor material provided by the invention, performance of the dibenzothiophene sulphone containing organic semiconductor material is characterized by differential thermal analysis. The result shows that the material has excellent thermal stability, and meanwhile, the material has good solubility and film-forming property. Through a spectral test, the maximum light emitting wavelength of the material is in a blue light range with wider energy gap. In addition, the light emitting material has dibenzothiophene sulphone, tetra-aryl silicon radicals in the structure, so that the material has better carrier transport performance.
Description
Technical field
The present invention relates to the organic semiconductor material field, relate in particular to a kind of dibenzothiophene sulfone organic semiconductor material and preparation method thereof and organic electroluminescence device of containing.
Background technology
Along with the development of information age, have efficient, energy-conservation, the organic EL display (OLEDs) of lightweight and the concern that the big area white-light illuminating more and more is subject to people.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 novel LED technology, have that active illuminating, light, thin, good contrast, energy consumption are low, organic electroluminescence device that can be made into the characteristics such as flexible device has proposed higher requirement to material.
1987, the Tang of U.S. Eastman Kodak company and VanSlyke reported the breakthrough in organic electroluminescent research.And to realize the application purposes such as panchromatic demonstration and illumination, luminescent device must have certain efficient and life-span.To cause device fewer for efficient, stable electricity at present, and the blue light material of high mobility, high thermal stability also relatively lacks.
Summary of the invention
What one of problem to be solved by this invention was to provide a kind of high mobility, high thermal stability contains dibenzothiophene sulfone organic semiconductor material.
A kind of dibenzothiophene sulfone organic semiconductor material that contains has following chemical structure of general formula:
In formula, A-is-F ,-CN or-NO
2
Two of problem to be solved by this invention is to provide a kind of preparation method who contains dibenzothiophene sulfone organic semiconductor material, comprises the steps:
S1, provide following compound:
Compound I:
Compound I I:
Or
Wherein, in compound formula II, A-is-F ,-CN or-NO
2
S2, in atmosphere of inert gases, 1: 2～1: 3 be dissolved in the organic solvent that contain catalyzer and alkaline solution with mol ratio Compound I and II, carry out Suzuki reaction 20～48h under 70～110 ℃ of reflux conditions, what make following chemical structure of general formula contains dibenzothiophene sulfone organic semiconductor material:
In the above-mentioned preparation method who contains dibenzothiophene sulfone organic semiconductor material, also comprise purification step:
S3, after step S2 reaction finishes, reaction solution is poured in the aqueous solution of saturated ammonium chloride, with dichloromethane extraction reaction solution three times, obtain organic phase; Subsequently organic phase with sodium chloride aqueous solution wash, dry, revolve and obtain crude product after steaming desolventizing, and crude product is through the silica gel column chromatography separating-purifying, what obtain at last purifying contains dibenzothiophene sulfone organic semiconductor material.
The above-mentioned preparation method who contains dibenzothiophene sulfone organic semiconductor material, in step S2, the mole dosage of described catalyzer is 0.001～0.1 times of Compound I mole dosage; Described organic palladium is tetrakis triphenylphosphine palladium, three (dibenzalacetone) two palladiums or two (triphenyl phosphorus) palladium chloride.
The above-mentioned preparation method who contains dibenzothiophene sulfone organic semiconductor material is characterized in that, in step S2, described alkaline solution is Cs
2CO
3Solution, K
2CO
3Solution, Na
2CO
3Solution or Li
2CO
3Solution; Described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
Three of problem to be solved by this invention is to provide a kind of organic electroluminescence device, its luminescent layer material comprise have a following chemical structure of general formula contain dibenzothiophene sulfone organic semiconductor material:
In formula, A-is-F ,-CN or-NO
2
The dibenzothiophene sulfone organic semiconductor material that contains provided by the invention scans by differential thermal analysis this performance that contains dibenzothiophene sulfone organic semiconductor material is characterized, and result shows that this material has excellent thermostability; Simultaneously, 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 wider energy gap; In addition, this luminescent material makes material have electronic transmission performance preferably due to the existence of thiophene in structure and four aryl silicon groups.
The preparation method who contains dibenzothiophene sulfone organic semiconductor material provided by the invention, technique is simple, and is easy to operate, and production technique is easy to control, and is convenient to produce promote.
Description of drawings
Fig. 1 is that embodiment 1 makes the fluorescence spectrum figure that contains dibenzothiophene sulfone organic semiconductor material (DCNSiF) film.
Fig. 2 is the structural representation of the organic electroluminescence device of embodiment 4.
Embodiment
The present embodiment a kind of contain the dibenzothiophene sulfone organic semiconductor material, have following chemical structure of general formula:
In formula, A-is that (F), cyano group (CN) or nitro (NO for fluorine atom
2) in any one.
Above-mentioned contain the dibenzothiophene sulfone the preparation method of organic semiconductor material, step is as follows:
S1, provide following compound:
Compound I:
Compound I I:
Or
Wherein, in compound formula II, A-is that (F), cyano group (CN) or nitro (NO for fluorine atom
2) in any one;
S2, (comprise nitrogen or argon gas etc.) in atmosphere of inert gases, 1: 2～1: 3 be dissolved in the organic solvent that contain catalyzer and alkaline solution with mol ratio Compound I and II, carry out Suzuki reaction 20～48h under 70～110 ℃ of reflux conditions, make structural formula and be
Compound, i.e. ASiF; Reaction formula is as follows:
Wherein, in above-mentioned preparation method's step S2, described catalyzer is that organic palladium is (as, tetrakis triphenylphosphine palladium (Pd (PPh
3)
4), three (dibenzalacetone) two palladium (Pd
2(dba)
3) or two (triphenyl phosphorus) palladium chloride (Pd (PPh
3)
2Cl
2)); The mole dosage of described catalyzer is 0.001～0.1 times of Compound I mole dosage; Described alkaline solution is the Cs of 2mol/L
2CO
3Solution, K
2CO
3Solution, Na
2CO
3Solution or Li
2CO
3Solution, and the volume number is 35ml～45ml; Described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
In the above-mentioned preparation method who contains dibenzothiophene sulfone organic semiconductor material, also comprise purification step:
S3, after step S2 reaction finishes, reaction solution is poured in the aqueous solution of saturated ammonium chloride, with the dichloromethane extraction reaction solution repeatedly, obtain organic phase; Subsequently organic phase with sodium chloride aqueous solution wash, dry, revolve and obtain crude product after steaming desolventizing, and crude product obtains the organic semiconductor material that contains phenanthroline of purifying at last through the silica gel column chromatography separating-purifying.
A kind of organic electroluminescence device, its luminescent layer material comprise have a following chemical structure of general formula contain dibenzothiophene sulfone organic semiconductor material:
In formula, A-is-F ,-CN or-NO
2
The machine semiconductor material that contains the dibenzothiophene sulfone provided by the invention, by differential thermal analysis scan to this kind contain the dibenzothiophene sulfone the performance of organic semiconductor material characterize, result shows that this material has excellent thermostability; Simultaneously, 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 wider energy gap; In addition, this luminescent material makes material have electronic transmission performance preferably due to the existence of thiophene in structure and four aryl silicon groups.
Four aryl silicon can effectively be blocked carbon carbon conjugated chain due to the existence of silicon, make compound have larger band-gap energy; Four aryl silicon are tetrahedron skeleton structures of rigidity simultaneously, help to improve the thermostability of material.And thiophene is the electron deficiency group, can improve the electronic transmission performance of material, and its group itself is also a plane rigid structure simultaneously, helps to improve the thermostability of material.The introducing of the electron-withdrawing groups such as cyano group, fluorine, nitro can improve the material electronics transmission performance equally.
The preparation method who contains dibenzothiophene sulfone organic semiconductor material provided by the invention, technique is simple, and is easy to operate, and production technique is easy to control, and is convenient to produce promote.
Below in conjunction with accompanying drawing, preferred embodiment of the present invention is described in further detail.
Embodiment 1
The present embodiment disclose structural formula following contain dibenzothiophene sulfone organic semiconductor material, namely 2,7-two (4-((4-cyano-phenyl) phenylbenzene silicon) phenyl) thiophene (DCNSiF)
The preparation of 2,7-two (4-((4-cyano-phenyl) phenylbenzene silicon) phenyl) thiophene (DCNSiF):
With 2; 7-dibromo thiophene 3mmol; 4-((4-cyano-phenyl) phenylbenzene silicon) phenylo boric acid 6.0mmol; tetrakis triphenylphosphine palladium 0.003mmol joins in reaction flask; vacuumize, after logical nitrogen circulation 3 times; make reaction system be in anaerobic state, under nitrogen protection, add the Na of tetrahydrofuran (THF) 50mL, 2mol/L
2CO
3Aqueous solution 35ml is heated to 70 ℃ of backflow Suzuki reaction 48h 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, through the silica gel column chromatography separating-purifying, obtain at last 2 of yellow-white, 7-two (4-((4-cyano-phenyl) phenylbenzene silicon) phenyl) thiophene solid product.
Productive rate: 90%.MALDI-TOF-MS：m/z 935(M
+)。
1H NMR(300MHz，CDCl
3，ppm)：δ＝8.26～8.20(t，4H)，δ＝7.92～7.88(m，6H)，δ＝7.69～7.43(m，32H)。。
Fig. 1 is the fluorescence spectrum figure that contains dibenzothiophene sulfone organic semiconductor material (DCNSiF) film that embodiment 1 makes; By in Fig. 1 as can be known its maximum emission wavelength be 441nm, at dark blue optical range, the material of main part that can be used as organic electrophosphorescenpolymer uses, and itself also can be used as luminescent material simultaneously and uses.
Embodiment 2
The present embodiment disclose structural formula following contain dibenzothiophene sulfone organic semiconductor material, namely 2,7-two (4-((the fluorine-based phenyl of 4-) phenylbenzene silicon) phenyl) thiophene (DFSiF)
The preparation of 2,7-two (4-((the fluorine-based phenyl of 4-) phenylbenzene silicon) phenyl) thiophene (DFSiF):
With 2; 7-dibromo thiophene 3mmol; 4-((the fluorine-based phenyl of 4-) phenylbenzene silicon) borate ester 6.4mmol; two (triphenyl phosphorus) palladium chloride 0.09mmol joins in reaction flask; vacuumize, after logical argon gas circulation 3 times; make reaction system be in anaerobic state, under argon shield, add the Cs of glycol dimethyl ether 50mL, 2mol/L
2CO
3Aqueous solution 40ml is heated to 90 ℃ of backflow Suzuki reaction 36h 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, through the silica gel column chromatography separating-purifying, obtain at last 2 of yellow-white, 7-two (4-((the fluorine-based phenyl of 4-) phenylbenzene silicon) phenyl) thiophene solid product.
Productive rate: 88%.MALDI-TOF-MS：m/z 921(M
+)。
1H NMR(300MHz，CDCl
3，ppm)：δ＝8.25～8.19(t，4H)，δ＝7.91～7.89(d，4H)，δ＝7.65～7.41(m，34H)。
Embodiment 3
The present embodiment disclose structural formula following contain dibenzothiophene sulfone organic semiconductor material, namely 2,7-two (4-((4-nitrophenyl) phenylbenzene silicon) phenyl) thiophene (DNO
2SiF)
2,7-two (4-((4-nitrophenyl) phenylbenzene silicon) phenyl) thiophene (DNO
2SiF) preparation:
With 2; 7-dibromo thiophene 3mmol; 4-((4-nitrophenyl) phenylbenzene silicon) phenylo boric acid 9mmol; three (dibenzalacetone) two palladium 0.3mmol join in reaction flask; vacuumize, after the mixed gas circulation of logical argon gas and nitrogen 3 times; make reaction system be in anaerobic state, under argon gas and nitrogen mixed gas protected, add the K of toluene 50mL, 2mol/L
2CO
3Aqueous solution 45ml is heated to 110 ℃ of backflow Suzuki 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, through the silica gel column chromatography separating-purifying, obtain at last 2 of yellow-white, 7-two (4-((4-nitrophenyl) phenylbenzene silicon) phenyl) thiophene solid product.
Productive rate: 92%.MALDI-TOF-MS：m/z 975(M
+)。
1H NMR(300MHz，CDCl
3，ppm)：δ＝8.39(d，4H)，δ＝8.27～8.21(t，4H)，δ＝7.91～7.90(d，4H)，δ＝7.69～7.44(m，30H)。
Table one and two makes for embodiment 1,2 and 3 contain dibenzothiophene sulfone organic semiconductor material test data of experiment:
Table one is to detect by thermogravimetric analyzer (TGA), analysis condition is nitrogen atmosphere, when sweep velocity is 10 ℃/min, the heat decomposition temperature of organic semiconductor material in the embodiment that obtains, its heat decomposition temperature more than (5% thermal weight loss), illustrates that materials has quite high thermostability up to 525 ℃.
The heat decomposition temperature of table one organic semiconductor material
| Compound | DCNSiF | DFSiF | DNO 2SiF |
| Heat decomposition temperature/℃ (5% thermal weight loss) | 525 | 503 | 531 |
Table two is electronic mobilities of organic semiconductor material in the above-described embodiment that records by the field-effect transistor method, and electronic mobility reaches 1.4 * 10
-5cm
2(Vs)
-1Above, illustrate that materials has carrier transmission performance preferably.
The field-effect electronic mobility of table two organic semiconductor material
| Compound | DCNSiF | DFSiF | DNO 2SiF |
| Electronic mobility/cm 2(Vs) -1 | 6.1×10 -5 | 1.4×10 -5 | 2.7×10 -5 |
Embodiment 4
The luminescent layer material of the organic electroluminescence device of the present embodiment adopt that embodiment 1 makes 2,7-two (4-((4-cyano-phenyl) phenylbenzene silicon) phenyl) thiophene (DCNSiF).Its preparation technology is as follows:
1, with ito glass spin coating photoresist material, exposure, development, chloroazotic acid etching, be etched into needed pattern and size, then the conductive glass that etching is good cleans, use successively each ultrasonic cleaning 15min such as pure water, acetone, ethanol, clean up and rear it is carried out oxygen plasma treatment, the oxygen plasma treatment time is 15min, and power is 35W, improves the surperficial work content of conductive glass with this;
2, ito glass is put into the organic vacuum cavity, (material is m-MTDATA:F4-TCNQ to stack gradually evaporation p-doping hole transmission layer on the ITO layer, thickness is 40nm), (material is DCNSiF to luminescent layer, thickness is 30nm), (material is Bphen to hole blocking layer, thickness is 10nm), (material is Bphen:Cs to n-doping electron transfer layer, in Cs doping Bphen, doping ratio is 10wt%; Thickness is 40nm);
3, then the substrate of step 2 is moved into metallic cavity, continue evaporation cathode layer magnesium silver alloys Mg:Ag (10: 1, wt%) 150nm, the Ag layer of last evaporation one deck 10nm;
After above-mentioned technique is completed, obtain organic electroluminescence device.
As shown in Figure 2, this organic electroluminescence device structure is: glass/ITO/m-MTDATA:F4-TCNQ/DCNSiF/Bphen/Bphen:Cs/Mg:Ag/Ag.
Should be understood that, above-mentioned statement for preferred embodiment of the present invention is comparatively detailed, can not therefore think the restriction to scope of patent protection of the present invention, and scope of patent protection of the present invention should be as the criterion with claims.
Claims (8)
1. one kind contains dibenzothiophene sulfone organic semiconductor material, it is characterized in that having following chemical structure of general formula:
In formula, A-is-F ,-CN or-NO
2
2. a preparation method who contains dibenzothiophene sulfone organic semiconductor material, is characterized in that, comprises the steps:
S1, provide following compound:
Compound I:
Compound I I:
Wherein, in compound formula II, A-is-F ,-CN or-NO
2
S2, in atmosphere of inert gases, 1: 2～1: 3 be dissolved in the organic solvent that contain catalyzer and alkaline solution with mol ratio Compound I and II, carry out Suzuki reaction 20～48h under 70～110 ℃ of reflux conditions, what make following chemical structure of general formula contains dibenzothiophene sulfone organic semiconductor material:
3. the preparation method who contains dibenzothiophene sulfone organic semiconductor material according to claim 2, is characterized in that, also comprises purification step:
S3, after step S2 reaction finishes, reaction solution is poured in the aqueous solution of saturated ammonium chloride, use the dichloromethane extraction reaction solution, the acquisition organic phase; Subsequently organic phase with sodium chloride aqueous solution wash, dry, revolve and obtain crude product after steaming desolventizing, and crude product is through the silica gel column chromatography separating-purifying, what obtain at last purifying contains dibenzothiophene sulfone organic semiconductor material.
4. according to claim 2 or 3 described preparation methods that contain dibenzothiophene sulfone organic semiconductor material, it is characterized in that, in step S2, described catalyzer is tetrakis triphenylphosphine palladium, three (dibenzalacetone) two palladiums or two (triphenyl phosphorus) palladium chloride.
5. the according to claim 2 or 3 described preparation methods that contain dibenzothiophene sulfone organic semiconductor material, is characterized in that, in step S2, the mole dosage of described catalyzer is 0.001～0.1 times of Compound I mole dosage.
6. the according to claim 2 or 3 described preparation methods that contain dibenzothiophene sulfone organic semiconductor material, is characterized in that, in step S2, described alkaline solution is Cs
2CO
3Solution, K
2CO
3Solution, Na
2CO
3Solution or Li
2CO
3Solution.
7. the according to claim 2 or 3 described preparation methods that contain dibenzothiophene sulfone organic semiconductor material, is characterized in that, in step S2, described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
8. an organic electroluminescence device, is characterized in that, the luminescent layer material of this organic electroluminescence device comprises the dibenzothiophene sulfone organic semiconductor material that contains claimed in claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104358267A CN103172651A (en) | 2011-12-22 | 2011-12-22 | Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011104358267A CN103172651A (en) | 2011-12-22 | 2011-12-22 | Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103172651A true CN103172651A (en) | 2013-06-26 |
Family
ID=48632903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011104358267A Pending CN103172651A (en) | 2011-12-22 | 2011-12-22 | Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103172651A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN104311588A (en) * | 2014-11-05 | 2015-01-28 | 武汉大学 | Silafluorene-based aggregation-induced emission molecule as well as preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565430A (en) * | 2007-12-31 | 2009-10-28 | 葛来西雅帝史派有限公司 | Organic electroluminescent compounds and organic light emitting diodes comprising the same |
| CN101688114A (en) * | 2007-07-05 | 2010-03-31 | 巴斯夫欧洲公司 | Organic light-emitting diodes comprising at least one disilyl compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophen |
| CN101712674A (en) * | 2009-11-13 | 2010-05-26 | 华南理工大学 | Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof |
| WO2011085781A1 (en) * | 2010-01-16 | 2011-07-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
-
2011
- 2011-12-22 CN CN2011104358267A patent/CN103172651A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101688114A (en) * | 2007-07-05 | 2010-03-31 | 巴斯夫欧洲公司 | Organic light-emitting diodes comprising at least one disilyl compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophen |
| CN101565430A (en) * | 2007-12-31 | 2009-10-28 | 葛来西雅帝史派有限公司 | Organic electroluminescent compounds and organic light emitting diodes comprising the same |
| CN101712674A (en) * | 2009-11-13 | 2010-05-26 | 华南理工大学 | Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof |
| WO2011085781A1 (en) * | 2010-01-16 | 2011-07-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
Non-Patent Citations (1)
| Title |
|---|
| 李业新等: "二苯并噻吩砜类化合物的合成和光学性能", 《济南大学学报》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN104311588A (en) * | 2014-11-05 | 2015-01-28 | 武汉大学 | Silafluorene-based aggregation-induced emission molecule as well as preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107954884B (en) | High glass transition temperature hole injection material and preparation and application thereof | |
| CN103664644A (en) | Organic semiconductor material containing aniline and preparation method thereof, and organic electroluminescence device | |
| CN102653546B (en) | Bipolarity Blue-light emitting host material and preparation method thereof and organic electroluminescence device | |
| CN103288811B (en) | Containing dibenzothiophene sulphone organic semiconductor material, its preparation method and organic electroluminescence device | |
| CN110396051B (en) | Organic small molecule hole injection/transport material and preparation method and application thereof | |
| CN103172651A (en) | Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device | |
| CN103172652A (en) | Tetraphenyl silicon containing organic semiconductor material and preparation method thereof and organic electroluminescent device | |
| CN103772364A (en) | Organic semiconductor material containing carbazole, preparation method thereof, and organic electroluminescent device | |
| CN102850320B (en) | Compound containing dibenzothiophene sulfone and preparation method and application thereof | |
| CN103897688A (en) | Organic electroluminescent material and preparation method thereof, and organic electroluminescent device | |
| CN102838585B (en) | Organic semiconductor material containing dibenzothiophene sulfone, and preparation method and application thereof | |
| CN112661743B (en) | Naphthothiodibenzofuran-based green light micromolecule and preparation method and application thereof | |
| CN103172630B (en) | Containing phenanthroline organic semiconductor material and preparation method thereof and organic electroluminescence device | |
| CN103044386B (en) | Bifluoranthene-containing organic semiconductor material as well as preparation method and application thereof | |
| CN103304557B (en) | Organic semiconducting materials containing spiral shell fluorenes and preparation method thereof and organic electroluminescence device | |
| CN103172624B (en) | Containing thiophene organic semiconductor material and preparation method thereof and organic electroluminescence device | |
| CN103172586B (en) | Han oxadiazole organic semiconductor material and preparation method thereof and organic electroluminescence device | |
| CN104003927A (en) | Organic electroluminescence phosphorescence host material, preparation method thereof and organic electroluminescence device | |
| CN103288730A (en) | Organic semiconductor material containing quinoline, preparation method of organic semiconductor material and organic electroluminescent device | |
| CN104073238A (en) | Organic electroluminescent material and preparation method thereof, and organic electroluminescent device | |
| CN103897689B (en) | Electroluminescent organic material and its preparation method and organic electroluminescence device | |
| CN110938085A (en) | Axis compound and preparation method and application thereof | |
| CN103159584B (en) | Bi-fluoranthene-containing organic semiconductor material, its preparation method and application | |
| CN103130784B (en) | A kind of organic semiconductor material containing pyridine and its preparation method and application | |
| CN103288825A (en) | Organic semiconductor material containing phenanthroline and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20130626 |