CN102295758A - Conjugated fractured hyperbranched polymer semiconductor photoelectric material, preparation method thereof, and application method thereof - Google Patents
Conjugated fractured hyperbranched polymer semiconductor photoelectric material, preparation method thereof, and application method thereof Download PDFInfo
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Abstract
The invention relates to a conjugated fractured hyperbranched polymer semiconductor photoelectric material, a preparation method thereof, and an application method thereof. The invention belongs to the scientific field of organic photoelectric materials. The material and the methods provided by the invention have important potential significance in fields such as light emitting diode, solar cell, phosphorescence host material, organic electricity storing material, porous material, and gas sensor. The conjugated fractured hyperbranched polymer semiconductor photoelectric material has a structure represented by the formula. The material has advantages of relatively high stability and simple synthetic route. The conjugated fractured hyperbranched polymer semiconductor photoelectric material is prepared through a Friedel-Crafts polymerization reaction catalyzed by boron trifluoride diethyl ether under room temperature. The method has advantages of cheap raw materials, simple operation, normal-temperature preparation, and high yield.
Description
Technical field
The present invention is specifically related to interrupt the hyperbranched polymer photoelectric semiconductor material with the synthetic fluorenes class conjugation of a kind of new polymerization process, with step that adopts in the building-up process and raw material, and relate to such material at organic electroluminescent, the application in the photoelectric fields such as dynamo-electric storage and phosphorescent light body material is arranged.
Background technology
From Tang research group of Kodak [Tang, C.W. in 1987; Van Slyke, S.A.Appl.Phys.Lett.1987,51,913.] and nineteen ninety univ cambridge uk [Burroughes, J.H.; Bradley, D.D.C.; Brown, A.B.; Marks, R.N.; Mackay, K.; Friend, R.H.; Burn, P.L.; Holmes, A.B.Nature1990,347,539.] delivered respectively since the film-type organic electroluminescence device made from organic and polymer fluorescent material (Organic Light-emitting Diodes) and polymer LED (Polymeric Light-emitting Diodes), organic flat pannel display becomes the demonstration product of the another generation marketization after liquid-crystal display.Meanwhile other organic electronics and photoelectronic industry comprise that field such as organic field-effect tube, organic solar batteries, nonlinear optics, bio-sensing and laser and nonlinear optical material are also just moving towards the marketization.Organic and the advantage plastic electronic product is that the material preparation cost is low, technology simple, has the snappiness and the plasticity-of commodity polymer.Therefore, develop the novel organic photoelectric information material of market potential and attracted the scientist of the different subjects of domestic and international many universities and the concern and the input of research institution and company with practicality.In the opto-electrical polymers material, hyperbranched polymer has characteristics such as simple, the low Intermolecular Forces of synthesis technique, higher spectrum stability and fluorescence quantum efficiency; Up to the present, the method for synthetic polymer photoelectric material commonly used has coupling polymerization reactions such as Suzuki, Stille, yet, the rare and metal toxicity of precious metal, problems such as reaction conditions strictness are restricting the development of polymerization process.Along with the green of whole chemical bound pair organic synthesis, environmental protection, sustainable, proposition that atom economy requires, develop novel polymerization process synthesize the opto-electrical polymers material become the important research direction of field of photovoltaic materials it
Therefore, the present invention proposes the Fu Ke polymerization process that a kind of conjugation of synthesis of super branched at room temperature interrupts polymer photoelectric material, fast, simply synthesized serial conjugation by this method and interrupted hyperbranched polymer, estimate these polymkeric substance at phosphorescent light body material, have photoelectric fields such as dynamo-electric storage medium that important use is arranged.
Summary of the invention
Technical problem: severe reaction conditions when synthesizing photoelectric material in order to overcome prior art, deficiencies such as heavy metal catalyst toxicity is big, price is expensive, the present invention proposes a kind of fluorenone derivatives cheap and easy to get, thienyl boric acid, carbazole, alkoxy benzene of utilizing and is direct material, with the boron trifluoride diethyl etherate is the catalyzer of polyreaction, goes on foot the method that the reaction with simple operations obtains photoelectric material by three.Resulting hyperbranched polymer has higher spectrum stability and calorifics stability, and expectation can be applied to phosphorescent light body material, photoelectric field such as dynamo-electric storage is arranged.Whole reaction system has that raw material is cheap, and step is simple, the reaction conditions gentleness, and product is easily purified, productive rate height, characteristics such as toxicity is low.
Technical scheme: the present invention interrupts the synthetic of polymer photoelectric material for the fluorenes class is hyperbranched conjugated.Technological operation is earlier the cheap raw material fluorenone derivatives to be carried out the back to modify, again new synthetic fluorenone derivatives is synthesized tertiary alcohol monomer by grignard reaction, then at room temperature, by the Fu Ke polyreaction, characteristics such as that the synthetic hyperbranched conjugated polymer semiconductor's photoelectric material that interrupts of fluorenes class, reaction have is simple to operate, environmental friendliness, productive rate height.Described material has following structure:
Compound-material I compound-material II
X is nitrogen or carbon atom in the formula; R is hydrogen or the oxyalkyl chain that contains 4-12 carbon atom; N is the concrete numeral among the 3-100 or wherein has the numeral of certain distribution;
Ar
1, Ar
2Be hydrogen or conjugation aromatic ring unit, Ar
1, Ar
2Can be identical or different, concrete preferred structure is as follows:
Described X is a carbon atom, and R is the saturated oxyalkyl chain that contains 8 carbon atoms, Ar
1Be thiophene or carbazole group, Ar
2During for benzene, then material I, II have following structure:
Compound-material III compound-material IV
Compound-material V compound-material VI
The preparation method that conjugation interrupts the hyperbranched polymer photoelectric semiconductor material is: at ambient temperature, to be dissolved in the methylene dichloride by grignard reaction synthetic Diarylfluorene tertiary alcohol monomer, be added drop-wise to then in the catalyzer boron trifluoride diethyl etherate that is dissolved in the methylene dichloride and carry out the Fu Ke polyreaction, react cancellation reaction after 2-24 hour, separation, purifying and obtain product; The solvent that reacts used is new distillatory methylene dichloride, and catalyzer is a boron trifluoride diethyl etherate, and dropping is that the tertiary alcohol is added drop-wise in the catalyzer in proper order, and reaction scheme is as follows:
Compound-material I
Compound-material II
Compound-material III, IV, V, VI's is synthetic by way of being: with the fluorenone derivatives of suzuki reaction synthesizing thiofuran modification, perhaps synthesize the fluorenone derivatives that carbazole is modified with ullmann reaction earlier, its synthetic route is as follows:
Wherein, X
1Be chlorine, bromine or iodine, Ar
1Be thiophene or carbazole.The condition of suzuki reaction is a lucifuge, anaerobic, and triphenyl phosphorus palladium/salt of wormwood/Potassium monofluoride, tetrahydrofuran (THF)/toluene, reacted 48 hours by 95 degrees centigrade; The condition of ullmann reaction is a lucifuge, anaerobic, and cuprous iodide, 2,2 '-dipyridyl, salt of wormwood, 1, the 2-dichlorobenzene, reacted 24 hours by 180 degrees centigrade.In anhydrous, anaerobic, airtight, under 55 degrees celsius, by grignard reaction synthesis of diaryl fluorenes class tertiary alcohol monomer.At ambient temperature, by Fu Ke polyreaction synthetic materials III, IV, V, VI.
This material is at organic electroluminescent, phosphorescent light body material, has in the dynamo-electric field of storage and uses.
Beneficial effect: patent of the present invention is discussed by fluorenone derivatives and is carried out the back modification, simply, high yield obtains the fluorenone derivatives modified with aromatic ring, obtain tertiary alcohol monomer with grignard reaction then, at room temperature, by the Fu Ke polyreaction, simple high yield synthesized the hyperbranched conjugated polymer semiconductor's photoelectric material that interrupts of fluorenes class.
Present method is with the simple high efficiency hyperbranched polymer photoelectric material that synthesized of new approach, this method meet sustainable, environmental protection that the epoch propose organic synthesis, atom economy requirement, can promote polymer semiconductor's material in the photoelectric functional material field, to use widely.
Description of drawings
Fig. 1 .9-is to the nucleus magnetic hydrogen spectrum figure of bromine octyloxy benzene-2-(thiophene-2-yl)-9 hydrogen-fluorenol,
Fig. 2 .9-is to bromine octyloxy benzene-2, the nucleus magnetic hydrogen spectrum figure of 7-(two thiophene-2-yl)-9 hydrogen-fluorenol,
Fig. 3 .9-is to the nucleus magnetic hydrogen spectrum figure of bromine octyloxy benzene-2-(carbazole-2-yl)-9 hydrogen-fluorenol,
Fig. 4 .9-is to bromine octyloxy benzene-2, the nucleus magnetic hydrogen spectrum figure of 7-(two carbazoles-2-yl)-9 hydrogen-fluorenol,
Fig. 5. the nucleus magnetic hydrogen spectrum figure of poly-2-thiophene-9-hydrogen octyloxy benzene,
Fig. 6. gather 2, the nucleus magnetic hydrogen spectrum figure of 7-two thiophene-9-hydrogen octyloxy benzene,
Fig. 7. the nucleus magnetic hydrogen spectrum figure of poly-2-carbazole 9-hydrogen octyloxy benzene,
Fig. 8. gather 2, the nucleus magnetic hydrogen spectrum figure of 7-two carbazoles-9-hydrogen octyloxy benzene,
Fig. 9. the thermogravimetric analysis figure of polymkeric substance.
Embodiment
For more particularly bright above-mentioned technical scheme, below we are example with described compound-material III, set forth the detailed process of synthetic method:
(1) by suzuki reaction Synthetic 2-thiophene Fluorenone; scheme is to add 2-bromine Fluorenone in flask; thienyl boric acid; triphenyl phosphorus palladium/salt of wormwood/Potassium monofluoride reacted after 30 minutes, injected tetrahydrofuran (THF)/toluene; in lucifuge, sealing; temperature 80-120 degree centigrade, under the nitrogen protection condition, backflow 36-48 hour.After reaction finishes, add the frozen water cancellation, filter, extraction filtrate merges organic layer, anhydrous MgSO
4Drying is revolved steaming except that desolvating and is obtained crude product, obtains yellow solid 2-thiophene Fluorenone after the column purification drying excessively, and productive rate is 80-90%.
(2) synthetic by grignard reaction to bromine octyloxy benzene-2-thiophene-2-base-9-hydrogen-fluorenol; operation is in flask; the 2-thiophene Fluorenone that is dissolved in the methylene dichloride is added drop-wise to Grignard reagent in the bromine magnesium octyloxy benzene; in sealing, temperature of reaction is 40-65 degree centigrade; under the nitrogen protection condition, reacted 8-24 hour.Reaction is used the saturated ammonium chloride solution cancellation after finishing, and extraction filtrate merges organic layer, anhydrous MgSO
4Drying is revolved steaming except that desolvating and is obtained crude product, obtains faint yellow solid to bromine octyloxy benzene-2-thiophene-9-hydrogen-fluorenol after the column purification drying excessively, and productive rate is 60-80%.
(3) by the synthetic poly-2-thiophene of Fu Ke polyreaction-9-hydrogen octyloxy benzene.In the single port flask, be dissolved in the methylene dichloride to bromine octyloxy benzene-2-thiophene-9-hydrogen-fluorenol, be added drop-wise under the room temperature in the methylene dichloride that is dissolved with the catalyzer boron trifluoride diethyl etherate, react after 2-24 hour, use the frozen water cancellation, extraction filtrate, merge organic layer, anhydrous MgSO
4Drying is revolved and is boiled off part methylene chloride solution.With obtaining poly-2-thiophene-9-hydrogen octyloxy benzene after methyl alcohol sedimentation, acetone extracting, the drying, productive rate is 60-70%.
Further specifically describe technical scheme of the present invention below in conjunction with embodiment, but these embodiment and unrestricted embodiments of the present invention.The present invention has multiple different embodiment, has more than to be limited to content described in this specification sheets.Those skilled in the art is under the situation of the present application spirit, and the scheme of being finished should be within the scope of the invention.
Embodiment comprises three-step reaction: the back modification of (one) fluorenone derivatives: in lucifuge, anaerobic, reaction is 36-48 hour under 95 degrees celsius with thienyl boric acid and fluorenone derivatives, obtains the fluorenone derivatives that highly purified thiophene is modified through filtering, purifying; In lucifuge, anaerobic, reaction is 18-24 hour under 180 degrees celsius with carbazole and fluorenone derivatives, obtains the fluorenone derivatives that highly purified carbazole is modified through filtering, purifying; (2) tertiary alcohol is synthetic: the fluorenone derivatives of thiophene or carbazole modification is dissolved in the methylene dichloride, slowly is added drop-wise in the freshly prepd Grignard reagent, reaction is 18 hours under 55 degrees celsius, obtains the highly purified tertiary alcohol through filtering, purifying; (3) polymkeric substance is synthetic: tertiary alcohol monomer is dissolved in the methylene dichloride, slowly is added drop-wise under the room temperature in the dichloromethane solution that is dissolved with catalyzer (boron trifluoride diethyl etherate), obtains conjugation after sedimentation, extracting, the drying and interrupts the hyperbranched polymer photoelectric material.
Synthesizing of embodiment 1:2-thiophene Fluorenone
In two mouthfuls of flasks of 100ml, adding 2-bromine Fluorenone (0.9g, 0.005mol, 1eq.), thienyl boric acid (5.00g, 38.8mmol), the triphenyl phosphorus palladium (0.50g, 5%mmol), tetrahydrofuran (THF)/toluene (50ml), in sealing, lucifuge, anaerobic, temperature of reaction is 95 degrees centigrade, under the nitrogen protection condition, reacts 30 minutes; (39ml 78mmol), continues reaction 48 hours to inject salt of wormwood/Potassium monofluoride then.What need replenish is tetrahydrofuran (THF)/toluene, and salt of wormwood/Potassium monofluoride all is the solution of handling through deoxidation, and concentration is 2mol/L.Reaction is poured the frozen water cancellation into after finishing, and filters, and extraction filtrate merges organic layer, anhydrous MgSO
4Drying revolves that steam removing desolvates obtains crude product, obtains fluffy yellow solid 2-thiophene Fluorenone after crossing the column purification drying with sherwood oil/methylene dichloride of 4:1.Isolated yield is 89%, this compound infrared, and nuclear-magnetism and mass-spectrometric data are as follows:
IR(KBr)v?3086，2920，1700，1600，1452.GC-MS(EI-m/z)：261.9(M
+).
1H?NMR(400MHz，CDCl
3，ppm)：δ7.88(s，1H)，7.71-7.65(m，2H)，7.49-7.46(t，J＝6.7Hz，3H)，7.37-7.36(d，J＝3.5Hz，1H)，7.32-7.26(t，J＝7.2Hz，2H)，7.11-7.01(t，J＝4.3Hz，1H).
13C?NMR(100MHz，CDCl
3，ppm)：δ193.59，144.21，143.12，142.96，135.40，134.87，134.31，131.53，128.99，128.25，125.44，124.40，123.71，121.45，121.43，120.76，120.35.
Embodiment 2:2,7-two carbazole Fluorenones synthetic
In two mouthfuls of flasks of 250ml, add 2, the 7-dibromo fluorenone (6.72g, 20mmol); carbazole (8.00g, 48mmol), cuprous iodide (9.12g; 48mmol), and salt of wormwood (16.60g, 120mmol); 2,2 '-dipyridyl (0.005g), 1; 10-F beautiful jade (0.005g), 1,2-dichlorobenzene (2ml); in sealing, lucifuge, anaerobic, temperature of reaction is 180 degrees centigrade, under the nitrogen protection condition, reacts 24 hours.After reaction finishes, add the dichloromethane solution cancellation, filter, extraction filtrate merges organic layer, anhydrous MgSO
4Drying revolves that steam removing desolvates obtains crude product, obtains faint yellow solid 2,7-two carbazole Fluorenones after crossing the column purification drying with 6: 1 sherwood oils and methylene dichloride.Isolated yield is 57%, this compound infrared, and nuclear-magnetism and mass-spectrometric data are as follows:
IR(KBr)v?3055，2958，2848，1720，1595，1475，GC-MS(EI-m/z)：510.0(M
+).
1H?NMR(400MHz，CDCl
3，ppm)：δ8.18-8.16(d，J＝7.7Hz，4H)，7.94-7.96(d，J＝1.7Hz，2H)，7.87-7.85(d，J＝7.8Hz，2H)，7.80-7.78(dd，J＝1.95Hz，J＝1.98Hz，2H)，7.47-7.46(m，8H)，7.36-7.32(m，4H).
13C?NMR(100MHz，CDCl
3，ppm)：δ191.86，142.41，140.42，138.97，136.26，133.05，126.25，123.74，121.86，120.53，109.74.
Embodiment 3: to bromine octyloxy benzene-2, and 7-(two thiophene-2-yl)-9 hydrogen-fluorenol synthetic
In the 250ml there-necked flask; in the 50ml methylene dichloride 2 will be dissolved in; 7-two thiophene Fluorenone (1.12g; 3.3mmol) slowly be added drop-wise to grignard reagent to bromine magnesium octyloxy benzene (2.65g by constant pressure funnel; 9.3mmol) in; in sealing, temperature of reaction is 55 degrees centigrade, under the nitrogen protection condition, reacts 18 hours.After reaction finishes, add the saturated ammonium chloride solution cancellation, filter, extraction filtrate merges organic layer, anhydrous MgSO
4Drying is revolved steaming except that desolvating and is obtained crude product, obtains white solid 9-to bromine octyloxy benzene-2,7-(thiophene-2-yl)-9 hydrogen-fluorenol after the mistake column purification drying with 2: 1 sherwood oil/methylene dichloride.Isolated yield is 79%, this compound infrared, and nuclear-magnetism and mass-spectrometric data are as follows:
IR(KBr)v?3495，3425，3097，3035，2916，2849)，1604，1580，1498.GC-MS(EI-m/z)：533.9(M+).1H?NMR(400MHz，CDCl3，ppm)：δ7.67-7.61(m，4H)，7.58-7.57(d，J＝1.2Hz，2H)，7.37-7.35(d，d，J＝2.1Hz，J＝2.1Hz，2H)，7.31-7.30(d，d，J＝1.1Hz，J＝1.2Hz，2H)，7.26(s，1H)，7.25-7.25(d，J＝1.0Hz，2H)，7.06-7.04(m，2H)，6.83-6.80(d，d，J＝2.1Hz，J＝2.1Hz，2H)，3.92-3.89(t，J＝6.5Hz，2H)，2.46(s，1H)，1.76-1.70(m，2H)，1.43-1.37(m，2H)，1.31-1.26(m，8H)，0.88-0.85(m，3H).13C?NMR(100MHz，CDCl3，ppm)：δ158.56，151.58，144.21，138.30，134.65，128.08，126.92，126.62，124.92，123.37，122.15，120.54，114.37，83.33，67.98，31.84，29.38，29.30，29.27，26.08，22.69，14.15.
Embodiment 4: gather the synthetic of 2-carbazole-9-hydrogen octyloxy benzene
In 100ml single port flask, with 2-(9-hydrogen-carbazole-9-yl)-9-(4-octyloxy benzene)-9-hydrogen-fluorenol (0.26g, 0.47mmol) be dissolved in methylene dichloride (25ml), be added drop-wise under the room temperature and be dissolved with the catalyzer boron trifluoride diethyl etherate (0.51ml in methylene dichloride 4.7mmol) (10ml), reacts after 2-24 hour, use the frozen water cancellation, extraction filtrate merges organic layer, anhydrous MgSO
4Drying is revolved and is boiled off part methylene chloride solution.With obtaining poly-2-carbazole-9-hydrogen octyloxy benzene after methyl alcohol sedimentation, acetone extracting, the drying.Isolated yield is 79%, this compound infrared, and nuclear magnetic data is as follows:
IR(KBr)v?3047，2916，2846，1604，1580，1500.
1H?NMR(400MHz，CDCl
3，ppm)：δ8.07-7.66(5H)，7.50-7.33(6H)，7.19-6.98(6H)，6.79-6.52(2H)，3.91-3.59(2H)，1.7841.61(2H)，1.38-1.27(10H)，0.88-0.75(3H).
13C?NMR(100MHz，CDCl
3，ppm)：δ206.95，158.06，154.14，152.27，140.68，139.21，137.84，137.38，136.73，129.20，127.97，127.57，126.40，125.94，124.47，123.26，121.29，120.35，119.93，114.26，109.87，83.43，67.94，65.07，31.82，30.95，29.37，26.06，22.66，14.12.
Claims (5)
1. a conjugation interrupts the hyperbranched polymer photoelectric semiconductor material, it is characterized in that this material has the fluorenes class hyperbranched polymer photoelectric material of following structure:
Compound-material I compound-material II
X is nitrogen or carbon atom in the formula; R is hydrogen or the oxyalkyl chain that contains 4-12 carbon atom; N is the concrete numeral among the 3-100 or wherein has the numeral of certain distribution;
Ar
1, Ar
2Be hydrogen or conjugation aromatic ring unit, Ar
1, Ar
2Can be identical or different, concrete preferred structure is as follows:
2. conjugation as claimed in claim 1 interrupts the hyperbranched polymer photoelectric semiconductor material, it is characterized in that described X is a carbon atom, and R is the saturated oxyalkyl chain that contains 8 carbon atoms, Ar
1Be thiophene or carbazole group, Ar
2During for benzene, then material I, II have following structure:
Compound-material III compound-material IV
Compound-material V compound-material VI
One kind according to claim 1 conjugation interrupt the preparation method of hyperbranched polymer photoelectric semiconductor material, it is characterized in that concrete preparation method is: at ambient temperature, to be dissolved in the methylene dichloride by grignard reaction synthetic Diarylfluorene tertiary alcohol monomer, be added drop-wise to then in the catalyzer boron trifluoride diethyl etherate that is dissolved in the methylene dichloride and carry out the Fu Ke polyreaction, react cancellation reaction after 2-24 hour, separation, purifying and obtain product; The solvent that reacts used is new distillatory methylene dichloride, and catalyzer is a boron trifluoride diethyl etherate, and dropping is that the tertiary alcohol is added drop-wise in the catalyzer in proper order, and reaction scheme is as follows:
Compound-material I
Compound-material II
4. preparation method who interrupts the hyperbranched polymer photoelectric semiconductor material as conjugation as described in the claim 2, it is characterized in that compound-material III, IV, V, VI's is synthetic by way of being: the fluorenone derivatives of using the modification of suzuki reaction synthesizing thiofuran earlier, perhaps with the fluorenone derivatives of the synthetic carbazole modification of ullmann reaction, its synthetic route is as follows:
Wherein, X
1Be chlorine, bromine or iodine, Ar
1Be thiophene or carbazole.The condition of suzuki reaction is a lucifuge, anaerobic, and triphenyl phosphorus palladium/salt of wormwood/Potassium monofluoride, tetrahydrofuran (THF)/toluene, reacted 48 hours by 95 degrees centigrade; The condition of ullmann reaction is a lucifuge, anaerobic, and cuprous iodide, 2,2 '-dipyridyl, salt of wormwood, 1, the 2-dichlorobenzene, reacted 24 hours by 180 degrees centigrade.In anhydrous, anaerobic, airtight, under 55 degrees celsius, by grignard reaction synthesis of diaryl fluorenes class tertiary alcohol monomer.At ambient temperature, by Fu Ke polyreaction synthetic materials III, IV, V, VI.
One kind according to claim 1 conjugation interrupt the application method of hyperbranched polymer photoelectric semiconductor material, it is characterized in that this material at organic electroluminescent, phosphorescent light body material, have in the dynamo-electric field of storage and use.
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| CN103193733A (en) * | 2013-04-20 | 2013-07-10 | 山西博士天地科技有限公司 | 2,7-di-(N-phenothiazinyl)fluorenone and preparation method thereof |
| CN105622901A (en) * | 2016-03-16 | 2016-06-01 | 南京邮电大学 | Interrupt conjugated type polymer semiconductor material and preparation method and application thereof |
| CN106893083A (en) * | 2017-02-15 | 2017-06-27 | 南京工业大学 | Two-dimentional conjugated polymer and its preparation method and application |
| KR20210113078A (en) * | 2020-03-05 | 2021-09-15 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Coating-type composition for forming organic film, patterning process, polymer, and method for manufacturing polymer |
| CN114920908A (en) * | 2022-05-27 | 2022-08-19 | 福州大学 | Organic conjugated polymer containing fluorenone and application thereof in alpha-ketoester synthesis |
| WO2023187020A1 (en) * | 2022-03-30 | 2023-10-05 | Sumitomo Chemical Co., Ltd | Monomer and light-emitting polymer |
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| CN103193733A (en) * | 2013-04-20 | 2013-07-10 | 山西博士天地科技有限公司 | 2,7-di-(N-phenothiazinyl)fluorenone and preparation method thereof |
| CN105622901A (en) * | 2016-03-16 | 2016-06-01 | 南京邮电大学 | Interrupt conjugated type polymer semiconductor material and preparation method and application thereof |
| CN106893083A (en) * | 2017-02-15 | 2017-06-27 | 南京工业大学 | Two-dimentional conjugated polymer and its preparation method and application |
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| KR20210113078A (en) * | 2020-03-05 | 2021-09-15 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Coating-type composition for forming organic film, patterning process, polymer, and method for manufacturing polymer |
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| WO2023187020A1 (en) * | 2022-03-30 | 2023-10-05 | Sumitomo Chemical Co., Ltd | Monomer and light-emitting polymer |
| CN114920908A (en) * | 2022-05-27 | 2022-08-19 | 福州大学 | Organic conjugated polymer containing fluorenone and application thereof in alpha-ketoester synthesis |
| CN114920908B (en) * | 2022-05-27 | 2023-04-21 | 福州大学 | Fluorenone-containing organic conjugated polymer and application thereof in synthesis of alpha-ketoester |
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