CN102093158A - Fluorene-anthracene compound for preparing luminescent materials and synthesis method thereof - Google Patents
Fluorene-anthracene compound for preparing luminescent materials and synthesis method thereof Download PDFInfo
- Publication number
- CN102093158A CN102093158A CN2010105677439A CN201010567743A CN102093158A CN 102093158 A CN102093158 A CN 102093158A CN 2010105677439 A CN2010105677439 A CN 2010105677439A CN 201010567743 A CN201010567743 A CN 201010567743A CN 102093158 A CN102093158 A CN 102093158A
- Authority
- CN
- China
- Prior art keywords
- anthracene
- fluorenes
- compound
- fluorene
- phenyl
- 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
Abstract
The invention relates to a fluorene-anthracene compound for preparing luminescent materials and a preparation method thereof. The structures of the compound are disclosed in the specification. The invention creatively connects anthracene with the 9th site of fluorene, and introduces a phenyl group and a naphthalene group into the fluorene unit, so that the conjugated system is further enlarged, thereby obtaining an ideal blue luminescent material. The method provided by the invention has the advantages of accessible raw materials and high yield, and is simple to operate; and the product prepared by the method provided by the invention has the advantage of stable structure, and is easy to store and suitable for large-scale production.
Description
Technical field
The present invention relates to a kind of fluorenes-anthracene compound and preparation method thereof, particularly a kind of fluorenes-anthracene compound of preparing luminescent material and preparation method thereof that can be used for.
Background technology
In the organic molecule luminescent material, anthracene class and fluorenes class are two kinds of materials that blue light luminous efficiency is higher.It is suitable to the thermal transition temperature that can improve material to studies show that anthracene and fluorenes ring, and thermostability improves, and luminous efficiency can not descend simultaneously, thereby obtains ideal luminescent material more.
In the research of having reported, fluorenes is connected 2 or 7 of the fluorenes that mostly occurs with anthracene, and 9 dianthranides of fluorenes research report as yet, its optical property remains further to be analyzed.The synthetic method of this compounds does not have report at present as yet.
Summary of the invention
One of purpose of the present invention is to provide a kind of new compound of material of blue light-emitting of two kinds of organic electroluminescence devices that can be used for making excellent property: 9-(2-phenyl)-9H-fluorenes-9-yl) anthracene and 9-(2-naphthyl)-9H-fluorenes-9-yl) anthracene.
Two of purpose of the present invention is to provide the synthetic method of this compound.
For achieving the above object, the reaction mechanism that the inventive method has adopted is:
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of 9-(2-phenyl-9H-fluorenes-9-yl) anthracene compound is characterized in that the structure of this compound is:
The characterization parameter of this compound is:
Chinese named: 9-(2-phenyl-9H-fluorenes-9-yl) anthracene
English name: 9-(2-phenyl-9H-fluoren-9-yl) anthracene
Molecular formula: C33H22
Molecular weight: 418
Outward appearance: white crystal
Fusing point: 230 degrees centigrade
UV spectrum maximum absorption band place wavelength location: 258 nanometers
Fluorescence radiation highest peak place wavelength: 424 nanometers, blue light
Proton nmr spectra (500MHz, CDCl
3) chemical shift (ppm of unit): 8.73 (d, 1H); 8.51 (s, 1H); 8.16 (d, 1H); 8.08 (d, 1H); 8.04((d, 1H); 7.94 (d, 1H); 7.73(d, 1H) 7.71(d, 1H); 7.67 (t, 1H); 7.66 (t, 1H); 7.46(d, 1H) 7.45 (t, 2H); 7.33(s, 1H); 7.31 (t, 3H); 7.26 (t, 3H); 7.18 (t, 1H); 6.88 (t, 1H); 6.75 (d, 1H); 6.60 (s, 1H).
Carbon-13 nmr spectra (125MHz, CDCl
3) chemical shift (ppm of unit): 149.86; 149.45; 141.16; 140.58; 140.00; 139.54; 132.43; 132.16; 131.90; 131.56; 129.84; 129.75; 128.96; 128.70; 128.03; 127.56; 127.28; 127.21; 126.68; 126.39; 125.87; 125.34; 124.94; 124.59; 124.01; 123.15; 120.88; 120.65; 49.12.
A kind of synthetic above-mentioned 9-(2-phenyl-9H-fluorenes-9-yl) method of anthracene is characterized in that this method has following steps: 2-phenyl-9-bromine fluorenes, anthracene are dissolved in the dithiocarbonic anhydride, add the Zinc Chloride Anhydrous of catalytic amount again, stir down and refluxed 24～48 hours; Be cooled to room temperature, remove zinc chloride, filtrate is concentrated the back separation and purification, get white crystal and be 9-(2-(4-fluorophenyl)-9H-fluorenes-9-yl) anthracene; The mol ratio of described 2-fluorophenyl-9-bromine fluorenes, anthracene is: 1:1～1.2.
A kind of 9-(2-naphthyl-9H-fluorenes-9-yl) anthracene compound is characterized in that the structure of this compound is:
Chinese named: 9-(2-naphthyl-9H-fluorenes-9-yl) anthracene
English name: 9-(2-(naphthalen-2-yl)-9H-fluoren-9-yl) anthracene
Molecular formula: C37H24
Molecular weight: 468
Outward appearance: white crystal
Fusing point: 290 degrees centigrade
Decomposition temperature: 450 degrees centigrade
Fluorescence efficiency: 90%(is in dichloromethane solvent)
UV spectrum maximum absorption band place wavelength location: 324 nanometers
Luminous highest peak place wavelength: 419 nanometers, blue light
Proton nmr spectra (500MHz, CDCl
3) chemical shift (ppm of unit): 8.74(d, 1H); 8.50 (s, 1H); 8.16 (d, 1H); 8.10 (d, 1H); 8.04((d, 1H); 7.93 (d, 1H); 7.89(s, 1); 7.83(d, 1H) 7.76(d, 3H); 7.59 (t, 1H); 7.58 (t, 2H); 7.46(t, 1H) 7.40 (t, 2H); 7.24(t, 1H); 7.18 (t, 1H); 7.07 (d, 1H); 7.18 (t, 1H); 6.88 (t, 1H); 6.77 (d, 1H); 6.61 (s, 1H).
Carbon-13 nmr spectra (125MHz, CDCl
3) chemical shift (ppm of unit): 149.85; 149.37; 140.35; 139.86; 139.52; 138.36; 133.54; 132.47; 132.33; 132.06; 131.79; 131.45; 129.74; 129.66; 128.85; 128.21; 128.09; 127.94; 127.52; 127.49; 127.19; 126.58; 125.79; 125.76; 125.63; 125.56; 125.27; 124.87; 124.85; 124.49; 123.92; 123.24; 120.87; 120.57; 49.03.
A kind of synthetic above-mentioned 9-(2-naphthyl-9H-fluorenes-9-yl) method of anthracene is characterized in that this method has following steps: 2-naphthyl-9-bromine fluorenes, anthracene are dissolved in the dithiocarbonic anhydride, add the Zinc Chloride Anhydrous of catalytic amount again, stir down and refluxed 24～48 hours; Be cooled to room temperature, remove zinc chloride, filtrate is concentrated the back separation and purification, get white crystal and be 9-(2-(4-fluorophenyl)-9H-fluorenes-9-yl) anthracene; The mol ratio of described 2-naphthyl-9-bromine fluorenes, anthracene is: 1:1～1.2.
The invention anthracene 9 with fluorenes are linked to each other, and in the fluorenes unit, introduce the group of phenyl and naphthalene.Make its conjugated system further enlarge, expectation obtains the ideal blue electroluminescent material.The inventive method raw material is easy to get, and is simple to operate, the productive rate height, and products therefrom Stability Analysis of Structures of the present invention, be easy to preserve, be fit to scale operation.
Embodiment
One, the preparation of 9-(2-phenyl-9H-fluorenes-9-yl) anthracene
Embodiment one:
1. prepare 2-phenyl-9-bromine fluorenes: in 50 milliliters the Erlenmeyer flask that reflux condensing tube is housed, add 2-benzene-9H-fluorenes-9 alcohol 0.77 gram, methylene dichloride 20mm, in constant pressure funnel, add the 3mm methylene dichloride, the phosphorus trichloride that adds 1mm immediately, reactant was reacting one hour at ice-water bath, naturally be warmed up to room temperature again, react stopped reaction after 12 hours.Reaction finishes back adding saturated sodium bicarbonate solution to room temperature, separatory, and drying is spin-dried for, separates with silica gel column chromatography, be developping agent with petrol ether/ethyl acetate=10:1, crystallization gets white crystal 0.69 gram, and productive rate is 72%.
2. preparation 9-(2-phenyl-9H-fluorenes-9-yl) anthracene adopts following steps: add 2-benzene-9-bromine fluorenes 0.64 gram in 50 milliliters the round-bottomed flask that reflux condensing tube is housed, anthracene 0.36 gram, zinc chloride 1.08g, 20 milliliters of dithiocarbonic anhydride.Reactant is stirring reaction stopped reaction after 24 hours under refluxing.Reaction finishes postcooling to room temperature, and suction filtration is removed zinc chloride, concentrated filtrate.The concentrated solution that obtains is separated with silica gel column chromatography, is developping agent with the sherwood oil, and the back gets white crystal 0.51 gram with the petrol ether/ethyl acetate recrystallization, and productive rate is 61%.
Embodiment two:
1. prepare 2-phenyl-9-bromine fluorenes: in 250 milliliters the Erlenmeyer flask that reflux condensing tube is housed, add 2-benzene-9H-fluorenes-9 alcohol 4,64 grams, methylene dichloride 120mm, in the 25mm constant pressure funnel, add the 10mm methylene dichloride, the phosphorus trichloride that adds 5mm immediately, reactant is warmed up to room temperature more naturally ice-water bath reaction one hour, reacts stopped reaction after 12 hours.Reaction finishes back adding saturated sodium bicarbonate solution to room temperature, separatory, and drying is spin-dried for, separates with silica gel column chromatography, be developping agent with petrol ether/ethyl acetate=10:1, crystallization gets white crystal 3,63 grams, and productive rate is 63%.
2. preparation 9-(2-phenyl-9H-fluorenes-9-yl) anthracene adopts following steps: 9-benzene in 250 milliliters the round-bottomed flask that reflux condensing tube is housed-9-bromine fluorenes 3.20 grams, anthracene 1.80 grams, zinc chloride 5.44g, 100 milliliters of dithiocarbonic anhydride.Reactant is stirring reaction stopped reaction after 24 hours under refluxing.Reaction finishes postcooling to room temperature, and suction filtration is removed chlorination zinc powder, concentrated filtrate.The concentrated solution that obtains is separated with silica gel column chromatography, is developping agent with the sherwood oil, and the back gets yellow-green colour crystal 2 .67 gram with the petrol ether/ethyl acetate recrystallization, and productive rate is 64%.
Embodiment three:
1. prepare 2-phenyl-9-bromine fluorenes: preparation 2-phenyl-9-bromine fluorenes: in 100 milliliters the Erlenmeyer flask that reflux condensing tube is housed, add 2-benzene-9H-fluorenes-9 alcohol 2.58 grams, methylene dichloride 50mm, in the 25mm constant pressure funnel, add the 5mm methylene dichloride, the phosphorus trichloride that adds 3mm immediately, reactant was reacting one hour at ice-water bath, naturally be warmed up to room temperature again, react stopped reaction after 12 hours.Reaction finishes back adding saturated sodium bicarbonate solution to room temperature, separatory, and drying is spin-dried for, separates with silica gel column chromatography, be developping agent with petrol ether/ethyl acetate=10:1, crystallization gets white crystal 1,92 gram, and productive rate is 60%.
2. preparation 9-(2-phenyl-9H-fluorenes-9-yl) anthracene adopts following steps: add 2-benzene-9-bromine fluorenes 1.6 grams in the round-bottomed flask that reflux condensing tube is housed of 100ml, anthracene 0.89 gram, zinc chloride 2.72g, 50 milliliters of dithiocarbonic anhydride.Reactant is stirring reaction stopped reaction after 24 hours under refluxing.Reaction finishes postcooling to room temperature, and suction filtration removes zinc chloride, concentrated filtrate.The concentrated solution that obtains is separated with silica gel column chromatography, is developping agent with the sherwood oil, and the back gets yellow-green colour crystal 1.03 grams with the petrol ether/ethyl acetate recrystallization, and productive rate is 50%.
Two, the preparation of 9-(2-naphthyl-9H-fluorenes-9-yl) anthracene.
Embodiment one:
1. prepare 2-naphthyl-9-bromine fluorenes: in 50 milliliters the Erlenmeyer flask that reflux condensing tube is housed, add 2-naphthalene-9H-fluorenes-9 alcohol 0.31 gram, methylene dichloride 24mm, in the 10mm constant pressure funnel, add the 5mm methylene dichloride, the phosphorus trichloride that adds 0.6mm immediately, reactant was reacting one hour at ice-water bath, naturally be warmed up to room temperature again, react stopped reaction after 12 hours.Reaction finishes back adding saturated sodium bicarbonate solution to room temperature, separatory, and drying is spin-dried for, separates with silica gel column chromatography, be developping agent with petrol ether/ethyl acetate=10:1, crystallization gets white crystal 0.23 gram, and productive rate is 63%.
2. prepare 10-(2-naphthalene-9H-fluorenes)-anthracene employing following steps: in 50 milliliters the round-bottomed flask that reflux condensing tube is housed, add 2-naphthalene-9-bromo-fluorenes 0.200 gram, anthracene 0.096 gram, zinc chloride 0.29g, 20 milliliters of dithiocarbonic anhydride.Reactant is stirring reaction stopped reaction after 24 hours under refluxing.Reaction finishes postcooling to room temperature, and suction filtration is removed zinc chloride, concentrated filtrate.The concentrated solution that obtains is separated with silica gel column chromatography, is developping agent with the sherwood oil, and the back gets white crystal 0.163 gram with the petrol ether/ethyl acetate recrystallization, and productive rate is 64%.
Embodiment two:
1. prepare 2-naphthyl-9-bromine fluorenes: in 100 milliliters the Erlenmeyer flask that reflux condensing tube is housed, add 2-naphthalene-9H-fluorenes-9 alcohol 0.74 gram, methylene dichloride 40mm, in the 10mm constant pressure funnel, add the 5mm methylene dichloride, the phosphorus trichloride that adds 0.8mm immediately, reactant was reacting one hour at ice-water bath, naturally be warmed up to room temperature again, react stopped reaction after 12 hours.Reaction finishes back adding saturated sodium bicarbonate solution to room temperature, separatory, and drying is spin-dried for, separates with silica gel column chromatography, be developping agent with petrol ether/ethyl acetate=10:1, crystallization gets white crystal 0.61 gram, and productive rate is 69%.
2. prepare 10-(2-naphthalene-9H-fluorenes)-anthracene employing following steps: 9-benzene in 100 milliliters the round-bottomed flask that reflux condensing tube is housed-9-bromine fluorenes 0.6025 gram, anthracene 0.300 gram, zinc chloride 1.8g, 50 milliliters of dithiocarbonic anhydride.Reactant is stirring reaction stopped reaction after 24 hours under refluxing.Reaction finishes postcooling to room temperature, and suction filtration is removed chlorination zinc powder, concentrated filtrate.The concentrated solution that obtains is separated with silica gel column chromatography, is developping agent with the sherwood oil, and the back gets yellow-green colour crystal 0.4330 gram with the petrol ether/ethyl acetate recrystallization, and productive rate is 57%.
Embodiment three:
1. prepare 2-naphthyl-9-bromine fluorenes: in 250 milliliters the Erlenmeyer flask that reflux condensing tube is housed, add 2-naphthalene-9H-fluorenes-9 alcohol 8,93 grams, methylene dichloride 120mm, in the 25mm constant pressure funnel, add the 10mm methylene dichloride, the phosphorus trichloride that adds 7mm immediately, reactant is warmed up to room temperature more naturally ice-water bath reaction one hour, reacts stopped reaction after 12 hours.Reaction finishes back adding saturated sodium bicarbonate solution to room temperature, separatory, and drying is spin-dried for, separates with silica gel column chromatography, be developping agent with petrol ether/ethyl acetate=10:1, crystallization gets white crystal 5.70 grams, and productive rate is 53%.
2. prepare 10-(2-naphthalene-9H-fluorenes)-anthracene employing following steps: in the round-bottomed flask that reflux condensing tube is housed of 250ml, add 2-naphthalene-9-bromine fluorenes 5.2757 grams, anthracene 2.5625 grams, zinc chloride 11.32g, 150 milliliters of dithiocarbonic anhydride.Reactant is stirring reaction stopped reaction after 24 hours under refluxing.Reaction finishes postcooling to room temperature, and suction filtration removes zinc chloride, concentrated filtrate.The concentrated solution that obtains is separated with silica gel column chromatography, is developping agent with the sherwood oil, and the back gets yellow-green colour crystal 2 .753 gram with the petrol ether/ethyl acetate recrystallization, and productive rate is 40%.
Remarks: the ultra-violet absorption spectrum and the fluorescence spectrum testing method of compound 9-(2-phenyl-9H-fluorenes-9-yl) anthracene and 9-(2-naphthyl-9H-fluorenes-9-yl) anthracene
1. the testing method of UV spectrum: compound is mixed with the dichloromethane solution of every milliliter of 1 microgram, and the cuvette that to get 3 milliliters of sectional areas of packing into again be 1 centimetre of 1 centimetre of * is used ultraviolet spectrophotometer, tests, and sweep limit is from 200 nanometer to 800 nanometers.
2. the fluorometric investigation method of emission wavelength: the dichloromethane solution that compound is mixed with every milliliter of 1 microgram, the cuvette that to get 3 milliliters of sectional areas of packing into again be 1 centimetre of 1 centimetre of *, use spectrophotofluorometer, test, earlier with 350 nano wave lengths as excitation wavelength, record a launching curve, again with the wavelength of this curve climax correspondence as emission wavelength, obtain an excitation curve, at last use the wavelength of this excitation curve climax correspondence again as excitation wavelength, for the second time obtain launching curve, with the emission wavelength of the pairing wavelength in the climax of this curve as the dichloromethane solution of every milliliter of this compound 1 microgram.
Claims (4)
1. anthracene compound 9-(2-phenyl-9H-fluorenes-9-yl) is characterized in that the structure of this compound is:
2. the method for anthracene synthetic 9-(2-phenyl according to claim 1-9H-fluorenes-9-yl), it is characterized in that this method has following steps: 2-phenyl-9-bromine fluorenes, anthracene are dissolved in the dithiocarbonic anhydride, the Zinc Chloride Anhydrous that adds catalytic amount again stirs down and refluxed 24～48 hours; Be cooled to room temperature, remove zinc chloride, filtrate is concentrated the back separation and purification, get white crystal and be 9-(2-(4-fluorophenyl)-9H-fluorenes-9-yl) anthracene; The mol ratio of described 2-fluorophenyl-9-bromine fluorenes, anthracene is: 1:1～1.2.
3. anthracene compound 9-(2-naphthyl-9H-fluorenes-9-yl) is characterized in that the structure of this compound is:
4. the method for anthracene synthetic 9-(2-naphthyl according to claim 1-9H-fluorenes-9-yl), it is characterized in that this method has following steps: 2-naphthyl-9-bromine fluorenes, anthracene are dissolved in the dithiocarbonic anhydride, the Zinc Chloride Anhydrous that adds catalytic amount again stirs down and refluxed 24～48 hours; Be cooled to room temperature, remove zinc chloride, filtrate is concentrated the back separation and purification, get white crystal and be 9-(2-(4-fluorophenyl)-9H-fluorenes-9-yl) anthracene; The mol ratio of described 2-naphthyl-9-bromine fluorenes, anthracene is: 1:1～1.2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105677439A CN102093158A (en) | 2010-12-01 | 2010-12-01 | Fluorene-anthracene compound for preparing luminescent materials and synthesis method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105677439A CN102093158A (en) | 2010-12-01 | 2010-12-01 | Fluorene-anthracene compound for preparing luminescent materials and synthesis method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102093158A true CN102093158A (en) | 2011-06-15 |
Family
ID=44126449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010105677439A Pending CN102093158A (en) | 2010-12-01 | 2010-12-01 | Fluorene-anthracene compound for preparing luminescent materials and synthesis method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102093158A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1686976A (en) * | 2005-03-17 | 2005-10-26 | 复旦大学 | Conjugated ramification material of fluorine containing anthracene and pyrene at 9th position, preparation method and application |
| JP4067414B2 (en) * | 2003-01-22 | 2008-03-26 | 三井化学株式会社 | Asymmetric substituted anthracene compound and organic electroluminescent device containing the asymmetric substituted anthracene compound |
| CN101817719A (en) * | 2010-01-21 | 2010-09-01 | 上海大学 | 9-fluorene-anthracene compound and synthesis method thereof |
-
2010
- 2010-12-01 CN CN2010105677439A patent/CN102093158A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4067414B2 (en) * | 2003-01-22 | 2008-03-26 | 三井化学株式会社 | Asymmetric substituted anthracene compound and organic electroluminescent device containing the asymmetric substituted anthracene compound |
| CN1686976A (en) * | 2005-03-17 | 2005-10-26 | 复旦大学 | Conjugated ramification material of fluorine containing anthracene and pyrene at 9th position, preparation method and application |
| CN101817719A (en) * | 2010-01-21 | 2010-09-01 | 上海大学 | 9-fluorene-anthracene compound and synthesis method thereof |
Non-Patent Citations (3)
| Title |
|---|
| 《光学学报》 20100731 肖立新等 "蓝色荧光小分子电致发光材料" 第30卷, 第7期 * |
| JING WANG ET AL: ""C-9 fluorenyl substituted anthracenes: a promising new family of blue luminescent materials"", 《ORGANIC LETTERS》 * |
| 肖立新等: ""蓝色荧光小分子电致发光材料"", 《光学学报》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107383094A (en) | A kind of novel chiral gathering induced luminescence material and its preparation method and application | |
| CN104649923B (en) | 1-Amino-12-hydroxy-3,4: 9,10-perylene n-butyl tetracarboxylate and synthesis method thereof | |
| CN107384374B (en) | A kind of aggregation-induced emission and mechanical cause enhancing luminescent material and preparation method | |
| CN107759504B (en) | Dual-phase organic fluorescent material with strong fluorescence in solid and liquid states and preparation method thereof | |
| CN106892800A (en) | A kind of preparation method and application of unactivated alkene hydrogen trifluoromethylation | |
| CN101817719B (en) | 9-fluorene-anthracene compound and synthesis method thereof | |
| CN111349109B (en) | Synthetic method of seven-element boron dipyrromethene fluorescent dye | |
| CN105837568B (en) | A kind of fluorenyl β carbolines class compound, its application and preparation method as luminous organic material and aggregation inducing Fluorescence Increasing material | |
| CN104004004B (en) | A kind of is the compound sending white light, the preparation and application of the isocyanide bridge chain gold of skeleton based on fluorenes | |
| CN103333204B (en) | One class 9, the synthetic method of 9 '-spirobifluorene derivative | |
| CN106146496A (en) | A kind of gulf district cyclization synthetic method of double imide derivative | |
| CN102093158A (en) | Fluorene-anthracene compound for preparing luminescent materials and synthesis method thereof | |
| CN104447336A (en) | Triptycene derivative and preparation method thereof | |
| CN107033175A (en) | Connected fluorine boron fluorescent dye oligomer of diacetylene and its preparation method and application | |
| CN106749076A (en) | O-hydroxy-phenyl azole derivative as organic blue light material application | |
| CN102863451A (en) | Preparation method and usage of triphenylamine molecule-containing chromene and naphthyridine fluorescent compound | |
| CN106905133B (en) | Spiro-fluorene-indene diketone compound and preparation method and application thereof | |
| CN102093882A (en) | Fluorine-containing electroluminescent material and preparation method thereof | |
| CN106242989A (en) | A kind of synthetic method of oxanilide analog derivative | |
| CN110963876A (en) | Preparation and purification method of 9, 10-substituted anthracene | |
| CN113045576B (en) | Construction method of pyrimido [1,2-b ] indazole parent nucleus | |
| CN101367742B (en) | 1-(4-amino-3, 5-di(phenylacetylene base)phenyl)ethanone and synthesis thereof | |
| Mao et al. | Highly efficient and regiospecific photocyclization of 2, 2′-diacyl bixanthenylidenes | |
| CN104003846B (en) | Dihydro indeno base fluorenes and synthetic method thereof | |
| CN102010365A (en) | 9-(9-(anthracene-10-yl)-9H-fluorene-2-yl)-9H-carbazole and synthetic method 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: 20110615 |