CN100386321C - Y-type second-order non-linear optical luminophor contg. triphenylamine, prepn. method and use thereof - Google Patents
Y-type second-order non-linear optical luminophor contg. triphenylamine, prepn. method and use thereof Download PDFInfo
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- CN100386321C CN100386321C CNB2006100188529A CN200610018852A CN100386321C CN 100386321 C CN100386321 C CN 100386321C CN B2006100188529 A CNB2006100188529 A CN B2006100188529A CN 200610018852 A CN200610018852 A CN 200610018852A CN 100386321 C CN100386321 C CN 100386321C
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Abstract
The present invention relates to a Y type second-order non-linear optical chromophore group containing triphenylamine groups, which has the following general formula, wherein in the general formula, X is oxygen or sulphur atoms; R is various electron withdrawing receptors, such as malononitrile, thiobarbituric acid, 3-phenyl-isoxazolone, 2-dicyanomethylene-3-cyano-4, 5, 5-trimethyl-2, 5-dihydrofuran, etc. The present invention can prepare the Y type second-order non-linear optical chromophore group containing triphenylamine groups from triphenylamine, phosphorus oxychloride, N, N-dimethylformamide, various electron withdrawing receptors, bromo furylmethyl triphenylphosphine or 2-methylthiophene and other reagents by a series of chemical reaction. The Y type second-order non-linear optical chromophore group containing triphenylamine groups as a second-order non-linear optical material can be practically applied to the aspects of remote communication, data storage, phase conjugation, etc.
Description
Technical field
The present invention relates to contain trianilino group Y type second-order nonlinear optical chromophore and its production and use.
Background technology
The construction of " information highway " has more and more caused the attention of national governments, economic party, society, is described as 21st century to give priority to industry.Current, rely on the development of electronics and microtronics technology, the mankind have set up the information network that quite improves with system., along with the progress of society, the existing information system still can't satisfy human to aspect requirements fast and accurately such as information processing, transmission, conversions.Simultaneously, because the physics limit of electronics itself---comprises the DENSITY LIMIT that electronics forms owing to the mutual interference mutually of elementary charge as the transmission speed limit (maximum value of electric transmission speed is 600km/s) of information carrier and element (functional unit)---, and " Moore's Law " can not be grown and exist in the youth, the carrier magnitude of electronic information technology can only be lucky position (Gb, promptly 10
9Bits).On the other hand, the speed of photon is fast more than electronics, the frequency of its frequency ratio wireless (as microwave) is much higher, replace electronics to come transmission information with photon, can accelerate information processing speed greatly, increase the capacity of process information, can overcome the bottleneck of microelectronics, more accurate, more efficient, farther apart from high-transmission information.Development for full optical information technology, nonlinear optics (NLO) is indispensable crucial subject, it has very important effect in practical fields such as high-speed light communication, optical information processing and photoelectronics, and nonlinear optical material obtains more and more widely attention in these Application for Field prospects.
The organic polymer nonlinear optical material have inorganic materials incomparable some advantages, such as super fast response speed, bigger nonlinear optical response, high light injury threshold values, excellent workability and low-k etc., and the organic polymer photoelectric functional material can be realized artificial controlled structure design and " cutting out " from molecular level.For these reasons and huge potential use, the research of organic polymer photoelectric functional material has caused the great attention of the national governments and the military.In order to reach the requirement of practicability, these materials not only will have big nonlinear optical response, and to satisfy device simultaneously to aspect requirements such as its transparency, thermostability and workabilitys, because the nonlinear optical properties of nonlinear optical active group (often claiming chromophoric group) molecule is wherein all at first depended in the nonlinear optical response of macromolecular material, so the synthetic second-order nonlinear optical chromophore molecule that has the big molecule single order hyperpolarizability (β) and the good optical transparency concurrently of design is one of challenging problem of tool for a long time always.
Summary of the invention
Purpose of the present invention just is to provide and contains trianilino group Y type second-order nonlinear optical chromophore and method for making and purposes.Such chromophoric group has big molecule single order hyperpolarizability (β), the good optical transparency and high thermostability concurrently, can be used as second-order non-linear optical materials and obtains practical application at aspects such as telecommunication, data storage, phase conjugations.
Technical scheme provided by the invention is: contain trianilino group Y type second-order nonlinear optical chromophore, have following general formula:
X is oxygen or sulphur atom in the formula, and R is the various acceptors that draw electronics, as malononitrile group, thiobarbituricacid base, 3-phenyl-isoxazole ketone group, 2-dicyano methylene radical-3-cyano group-4,5,5-trimethylammonium-2, electron-withdrawing groups such as 5-dihydrofuran base.
The present invention also provides the method for making of above-mentioned second-order nonlinear optical chromophore, with triphenylamine and N, dinethylformamide and phosphorus oxychloride were at 80-150 ℃ of reaction times 8-20 hour, make the triphenylamine dialdehyde, wherein triphenylamine, phosphorus oxychloride, N, the mol ratio of dinethylformamide is 1: 3.1～5.9: 6.1～9.9; Triphenylamine dialdehyde and bromo furan food in one's mouth methyl triphenyl phosphine or bromo thiophene methyl triphenyl phosphine were 10-50 ℃ of reaction 18-40 hour then, make vinyl triphenylamine furans or vinyl triphenylamine thiophene, wherein the mol ratio of triphenylamine dialdehyde and bromo furan methyl triphenyl phosphine or bromo thiophene methyl triphenyl phosphine is 1: 2.0～3.0; Vinyl triphenylamine furans and N, dinethylformamide and phosphorus oxychloride were 60-120 ℃ of reaction 0.5-4 hour, make vinyl triphenylamine Furan Aldehydes, therein ethylene base triphenylamine furans, N, the mol ratio of dinethylformamide, phosphorus oxychloride is 1: 5.1～7.9: 5.1～7.9; Perhaps vinyl triphenylamine thiophene and N, dinethylformamide and phosphorus oxychloride were 60-120 ℃ of reaction 0.5-6 hour, make vinyl triphenylamine thiophene aldehyde, therein ethylene base triphenylamine thiophene, N, the mol ratio of dinethylformamide, phosphorus oxychloride is 1: 4.1～6.5: 4.1～6.5; Be raw material with vinyl triphenylamine Furan Aldehydes or vinyl triphenylamine thiophene aldehyde at last, with propane dinitrile, thiobarbituricacid, 3-phenyl-isoxazolidinones or 2-dicyano methylene radical-3-cyano group-4,5,5-trimethylammonium-2, the 5-dihydrofuran was 30-120 ℃ of reaction 0.3-8 hour, make the described trianilino group Y type second-order nonlinear optical chromophore that contains of claim 1, therein ethylene base triphenylamine Furan Aldehydes or vinyl triphenylamine thiophene aldehyde and propane dinitrile, thiobarbituricacid, 3-phenyl-isoxazolidinones or 2-dicyano methylene radical-3-cyano group-4,5,5-trimethylammonium-2, the mol ratio that 5-dihydro furan is fed is 1: 1～2.3.
The trianilino group Y type second-order nonlinear optical chromophore that contains of the present invention can be used as the practical application of second-order non-linear optical materials at aspects such as telecommunication, data storage, phase conjugations.
The invention has the advantages that:
1. the present invention contains trianilino group Y type second-order nonlinear optical chromophore and has optical transparence preferably, compare with the aniline analogue, its maximum absorption wavelength violet shift the 29-45 nanometer, this phenomenon is more rare.
2. the present invention contains trianilino group Y type second-order nonlinear optical chromophore and has higher second-order nonlinear optical property (the single order hyperpolarizability of Id and IId is followed successively by 1023 and 1091 * 10 in example 1 and the example 2
-30Esu).
3. the invention describes the preparation that contains trianilino group Y type second-order nonlinear optical chromophore, enriched the content of second-order nonlinear optical chromophore research, expanded second-order nonlinear optical chromophore to a certain extent and become chemical method and mentality of designing.
Embodiment
Embodiment 1:
When X was Sauerstoffatom, synthetic route was as follows:
Synthetic method is:
Synthesizing of triphenylamine dialdehyde (compound 1)
With phosphorus oxychloride POCl
3Join among the DMF, reaction system is with the ice-water bath cooling and completely cut off moisture.Stir under the room temperature after 1 hour, add triphenylamine.Keep reaction 12 hours at 120 ℃, with (volume is 10-15 a times of reaction soln) in the mixture impouring frozen water, add the neutralization of 20%NaOH solution, there is yellow solid to separate out, thick product is with the silica gel chromatographic column (eluent: ethyl acetate: sherwood oil=1: 2) of purifying, get the glassy yellow solid, be the triphenylamine dialdehyde.Wherein triphenylamine, phosphorus oxychloride, N, the mol ratio of dinethylformamide is 1: 3.1～5.9: 6.1～9.9.142～143 ℃ of fusing points.IR：1692cm
-1(C＝O)。
Synthesizing of compound 2
Taking by weighing bromo furan methyl triphenyl phosphine adds in the Schlenk pipe.Under nitrogen protection, add the new tetrahydrofuran (THF) (THF) (quality is 7 times of bromo furan methyl triphenyl phosphine) that steams; add potassium tert.-butoxide then; drop into triphenylamine dialdehyde (1) again; stirring at room 24h; pour reaction solution in the distilled water (volume is 4 times of reaction solution); use chloroform extraction after stirring 2h, add anhydrous magnesium sulfate (quality is 10 times of triphenylamine dialdehyde) dried overnight.Revolving and remove chloroform, is that 1: 1 chloroform and sherwood oil is that eluent carries out column chromatography with volume ratio, obtains the reddish-brown solid, is product compound 2 after the vacuum-drying.The mol ratio that triphenylamine dialdehyde and bromo furan are fed methyl triphenyl phosphine, potassium tert.-butoxide is 1: 2.0～3.0: 3.1～3.7.
1H-NMR(CDCl
3)δ(ppm)：7.37-7.32(t，6H)，7.12(d，J＝7.2Hz，2H)，7.06-6.95(m，9H)，6.78(d，J＝16.5Hz，2H)，6.41(s，2H)，6.31(s，2H)。
Synthesizing of compound 3
Take by weighing compound 2, with 1 of new steaming, 2-ethylene dichloride dissolving (quality is 60 times of compound 2).Under nitrogen protection, in a there-necked flask, successively add new DMF and phosphorus oxychloride of steaming.The dichloroethane solution of raw material is joined (ice bath) in the there-necked flask.Stirring at room 1h is heated to ethylene dichloride backflow 2h then.Reaction solution is poured in the saturated solution of sodium carbonate of ice (volume is 4 times of reaction solution), used CHCl
3Extraction obtains orange red organic phase, adds (quality is 10 times of compound 2) anhydrous sodium sulfate drying and spends the night.Revolve and desolventize, carry out column chromatography with the chloroform give eluent.Obtain the red solid powder, be product compound 3 after the vacuum-drying.Wherein compound 2, N, the mol ratio of dinethylformamide, phosphorus oxychloride is 1: 5.1～7.9: 5.1～7.9.IR：1658cm
-1(C＝O)。
Chromophoric group Ia's is synthetic
In a 100ml round-bottomed flask, add aldehyde 3, add ethanol (quality is 300 times of compound 3) dissolving again.Propane dinitrile is added reaction soln, add three piperidines of catalyzer then, be warming up to 80 ℃, stir 2h.Revolve and remove ethanol, with CHCl
3For eluent carries out column chromatography.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain dark red crystallite chromophoric group Ia.Fusing point: 138-140 ℃.Wherein the mol ratio between aldehyde 3 and the propane dinitrile is 1: 1～2.3.IR：2221cm
-1(C≡N)。UV-Vis (chloroform, λ max): 544 nanometers.
Chromophoric group Ib's is synthetic
In a 100ml round-bottomed flask, add aldehyde 3, add ethanol (quality is 400 times of compound 3) dissolving again.The sulfo-veronal is added reaction soln, add three piperidines of catalyzer then, stirring at room 3h.Revolve and remove ethanol, with CHCl
3For eluent carries out column chromatography.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain dark blue black crystallite, be product chromophoric group Ib.Wherein the mol ratio between aldehyde 3 and the sulfo-veronal is 1: 1～2.3.Fusing point: 282-283 ℃.IR：1660cm
-1(C＝O)。UV-Vis (chloroform, λ max): 602 nanometers.
Chromophoric group Ic's is synthetic
In a 100ml round-bottomed flask, add aldehyde 3, add ethanol (quality is 350 times of compound 3) dissolving again.The phenyl-isoxazole oxazolone is added reaction soln, add three piperidines of catalyzer then, be warming up to 80 ℃, stir 4h.Revolve and remove ethanol, with CHCl
3For eluent carries out column chromatography.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain dark blue purple crystallite, be product chromophoric group Ic.Wherein the mol ratio between aldehyde 3 and the phenyl-isoxazole oxazolone is 1: 1～2.3.Fusing point: 170-172 ℃.IR：1739cm
-1(C＝O)。UV-Vis (chloroform, λ max): 577 nanometers.
Chromophoric group Id's is synthetic
In a 100ml round-bottomed flask, add aldehyde 3, add ethanol (quality is 500 times of compound 3) dissolving again.With 2-dicyano methylene radical-3-cyano group-4,5,5-trimethylammonium-2,5-dihydrofuran (TCF) adds reaction soln, adds three piperidines of catalyzer then, is warming up to 80 ℃, stirs 4h.Revolve and remove ethanol, with CHCl
3: ethyl acetate=20: 3 is carried out column chromatography for eluent.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain dark blue black crystallite, be product chromophoric group Id.Wherein the mol ratio between aldehyde 3 and the TCF is 1: 1～2.3.Fusing point: 210-212 ℃.IR：2226cm
-1(C≡N)。UV-Vis (chloroform, λ max): 621 nanometers.
Embodiment 2:
When X was sulphur atom, synthetic route was as follows:
Synthetic method is:
The preparation of bromo thiophene methyl triphenyl phosphine
(5.01g 50mmol), adds in the 250ml round-bottomed flask, adds tetracol phenixin 150ml then, and (10.7g, 60mmol), BPO powder 0.1g is heated to CCl to the NBS powder to take by weighing the 2-thiotolene
4Backflow 2h, reaction solution is gradually become than deep yellow by pale yellow solution.With reacting liquid filtering and use CCl
4The washing filter residue is collected gained CCl
4Solution revolves except that CCl
4Obtain yellow oily liquid, remove water-soluble impurity, use CHCl to wherein adding entry
3Extraction adds anhydrous Na
2SO
4Dried overnight.Elimination Na
2SO
4, the gained yellow solution is changed in the 250ml flask, add PPh
3(10.7g, 50mmol) and CHCl
3100ml, heated and stirred is to CHCl
3Reflux, stop heating behind the reaction 2h.A large amount of white solids appear in the bottle wall in the reflux course, and solution colour shoals.Filter and use a small amount of CHCl
3Washed product obtains white solid powdery product bromo thiophene methyl triphenyl phosphine.
Synthesizing as described in example 1 above of triphenylamine dialdehyde (compound 1).
Synthesizing of compound 4
Bromo thenyl group triphenylphosphine is added in the Schlenk pipe.Under logical condition of nitrogen gas,, add potassium tert.-butoxide, stirs adding triphenylamine dialdehyde (1) after ten minutes to wherein injecting the new THF (quality is 7 times of bromo thenyl group triphenylphosphine) of steaming.Stirring at room 24h pours reaction solution in the distilled water (volume is 3.5 times of THF) into, uses chloroform extraction behind the stirring 2h, adds anhydrous sodium sulphate (quality is 10 times of triphenylamine dialdehyde) dried overnight.Revolving and remove chloroform, is that 1: 1 chloroform and sherwood oil is that eluent carries out column chromatography with volume ratio, obtains the reddish-brown solid, is product after the vacuum-drying, compound 4.Wherein, the mol ratio of triphenylamine dialdehyde and bromo furan methyl triphenyl phosphine, potassium tert.-butoxide is 1: 2.0～3.0: 3.1～3.7.
1H-NMR(CDCl
3)δ(ppm)：7.34(d，J＝8.7Hz，4H)，7.30-7.26(m，5H)，7.14(d，J＝6.6Hz，2H)，7.07(d，J＝8.16Hz，4H)，7.03-6.95(m，6H)，6.88(d，J＝16.2Hz，2H)。
Synthesizing of compound 5
Take by weighing compound 4, with 1 of new steaming, 2-ethylene dichloride dissolving (quality is 45 times of compound 4).Under logical condition of nitrogen gas, in a there-necked flask, successively add new DMF of steaming and phosphorus oxychloride.Dichloroethane solution with 4 adds in the there-necked flask (ice bath).Stirring at room 1h is heated to ethylene dichloride backflow 3h then.Reaction solution is poured in the saturated solution of sodium carbonate of ice, used CHCl
3The organic layer that extraction obtains adds anhydrous sodium sulphate (quality is for changing 10 times that contain thing 4) dried overnight.Revolve and desolventize, carry out column chromatography with the chloroform give eluent.Obtain orange red pressed powder, after the vacuum-drying, be product, compound 5.Wherein compound 4, N, the mol ratio of dinethylformamide, phosphorus oxychloride is 1: 4.1～6.5: 4.1～6.5.IR：1658cm
-1(C＝O)。
Chromophoric group Ha's is synthetic
In a 100ml round-bottomed flask, add compound 5, add ethanol (quality is 300 times of compound 5) dissolving again.Propane dinitrile is added reaction soln, add three piperidines of catalyzer then, stirring at room 3h.Revolve and remove ethanol, with CHCl
3For eluent carries out column chromatography.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain the dark red crystallite, be product chromophoric group IIa.Wherein the mol ratio between aldehyde 5 and the propane dinitrile is 1: 1～2.3.Fusing point: 183-184 ℃.IR：2220cm
-1(C≡N)。UV-Vis (chloroform, λ max): 548 nanometers.
Chromophoric group IIb's is synthetic
In a 100ml round-bottomed flask, add aldehyde 5, add ethanol (quality is 360 times of compound 5) dissolving again.The sulfo-veronal is added reaction soln, add three piperidines of catalyzer then, be warming up to 80 ℃, stir 4h.Revolve and remove ethanol, with CHCl
3For eluent carries out column chromatography.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain dark blue purple crystallite, be product chromophoric group IIb.Wherein the mol ratio between aldehyde 5 and the sulfo-veronal is 1: 1～2.3.Fusing point: 266-268 ℃.IR：1656cm
-1(C＝O)。UV-Vis (chloroform, λ max): 601 nanometers.
Chromophoric group IIc's is synthetic
In a 100ml round-bottomed flask, add aldehyde 5, add ethanol (quality is 360 times of compound 5) dissolving again.The phenyl-isoxazole oxazolone is added reaction soln, add three piperidines of catalyzer then, be warming up to 80 ℃, stir 3h.Revolve and remove ethanol, with CHCl
3For eluent carries out column chromatography.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain dark blue purple crystallite, be product chromophoric group IIc.Wherein the mol ratio between aldehyde 5 and the phenyl-isoxazole oxazolone is 1: 1～2.3.Fusing point: 165-167 ℃.IR：1737cm
-1(C＝O)。UV-Vis (chloroform, λ max): 569 nanometers.
Chromophoric group IId's is synthetic
In a 100ml round-bottomed flask, add aldehyde 5, add ethanol (quality is 480 times of compound 5) dissolving again.TCF is added reaction soln, add three piperidines of catalyzer then, be warming up to 80 ℃, stir 4h.Revolve and remove ethanol, with CHCl
3: ethyl acetate=20: 3 is carried out column chromatography for eluent.With the crude product CHCl that obtains
3Carry out recrystallization with hexanaphthene, obtain dark blue black crystallite, be product chromophoric group IId.Rubbing than being 1: 1～2.3 between aldehyde 5 and the TCF wherein.Fusing point: 200-202 ℃.IR：2226cm
-1(C≡N)。UV-Vis (chloroform, λ max): 618 nanometers.
Claims (3)
1. contain trianilino group Y type second-order nonlinear optical chromophore, its general structure is:
X is oxygen or sulphur atom in the formula, and R is selected from following electron-withdrawing group: malononitrile group, thiobarbituricacid base, 3-phenyl-isoxazole ketone group, 2-dicyano methylene radical-3-cyano group-4,5,5-trimethylammonium-2,5-dihydrofuran base.
2. the described method for making that contains trianilino group Y type second-order nonlinear optical chromophore of claim 1, it is characterized in that: with triphenylamine and N, dinethylformamide and phosphorus oxychloride were at 80-150 ℃ of reaction times 8-20 hour, make the triphenylamine dialdehyde, wherein triphenylamine, phosphorus oxychloride, N, the mol ratio of dinethylformamide is 1: 3.1～5.9: 6.1～9.9; Triphenylamine dialdehyde and bromo furan methyl triphenyl phosphine or bromo thiophene methyl triphenyl phosphine were 10-50 ℃ of reaction 18-40 hour then, make vinyl triphenylamine furans or vinyl triphenylamine thiophene, wherein the mol ratio of triphenylamine dialdehyde and bromo furan methyl triphenyl phosphine or bromo thiophene methyl triphenyl phosphine is 1: 2.0～3.0; Vinyl triphenylamine furans and N, dinethylformamide and phosphorus oxychloride were 60-120 ℃ of reaction 0.5-4 hour, make vinyl triphenylamine Furan Aldehydes, therein ethylene base triphenylamine furans, N, the mol ratio of dinethylformamide, phosphorus oxychloride is 1: 5.1～7.9: 5.1～7.9; Perhaps vinyl triphenylamine thiophene and N, dinethylformamide and phosphorus oxychloride were 60-120 ℃ of reaction 0.5-6 hour, make vinyl triphenylamine thiophene aldehyde, therein ethylene base triphenylamine thiophene, N, the mol ratio of dinethylformamide, phosphorus oxychloride is 1: 4.1～6.5: 4.1～6.5; Be raw material with vinyl triphenylamine Furan Aldehydes or vinyl triphenylamine thiophene aldehyde at last, with propane dinitrile, thiobarbituricacid, 3-phenyl-isoxazolidinones or 2-dicyano methylene radical-3-cyano group-4,5,5-trimethylammonium-2, the 5-dihydrofuran was 30-120 ℃ of reaction 0.3-8 hour, make the described trianilino group Y type second-order nonlinear optical chromophore that contains of claim 1, therein ethylene base triphenylamine Furan Aldehydes or vinyl triphenylamine thiophene aldehyde and propane dinitrile, thiobarbituricacid, 3-phenyl-isoxazolidinones or 2-dicyano methylene radical-3-cyano group-4,5,5-trimethylammonium-2, the mol ratio of 5-dihydrofuran are 1: 1～2.3.
3. the described trianilino group Y type second-order nonlinear optical chromophore that contains of claim 1 is in telecommunication, data storage or phase conjugation Application for Field.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2946343A1 (en) * | 2009-06-09 | 2010-12-10 | Commissariat Energie Atomique | ORGANIC TYPE N SEMICONDUCTORS INCLUDING AT LEAST TWO 2-DICYANOMETHYLENE-3-CYABO-2,5-DIHYDROFURAN GROUPS |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103709197B (en) * | 2014-01-17 | 2015-11-04 | 四川大学 | Salicylaldehyde-TCF derivative replaced and its production and use |
| CN111040186B (en) * | 2019-12-27 | 2020-11-17 | 华中科技大学 | AB2Second-order nonlinear optical hyperbranched polymer, and preparation and application thereof |
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| JPH10330361A (en) * | 1997-06-03 | 1998-12-15 | Doujin Kagaku Kenkyusho:Kk | Triphenylamine derivative |
| CN1557906A (en) * | 2004-01-29 | 2004-12-29 | 复旦大学 | Red organic electroluminescent materials and method for preparing same |
| CN1706909A (en) * | 2004-06-11 | 2005-12-14 | 中国科学院化学研究所 | Host red luminous material with charge transferring structure and its prepn and application |
| CN1740171A (en) * | 2005-09-06 | 2006-03-01 | 武汉大学 | Second order non-linear optical chromophore containing indolyl radical and its prepn and application |
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2006
- 2006-04-21 CN CNB2006100188529A patent/CN100386321C/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10330361A (en) * | 1997-06-03 | 1998-12-15 | Doujin Kagaku Kenkyusho:Kk | Triphenylamine derivative |
| CN1557906A (en) * | 2004-01-29 | 2004-12-29 | 复旦大学 | Red organic electroluminescent materials and method for preparing same |
| CN1706909A (en) * | 2004-06-11 | 2005-12-14 | 中国科学院化学研究所 | Host red luminous material with charge transferring structure and its prepn and application |
| CN1740171A (en) * | 2005-09-06 | 2006-03-01 | 武汉大学 | Second order non-linear optical chromophore containing indolyl radical and its prepn and application |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2946343A1 (en) * | 2009-06-09 | 2010-12-10 | Commissariat Energie Atomique | ORGANIC TYPE N SEMICONDUCTORS INCLUDING AT LEAST TWO 2-DICYANOMETHYLENE-3-CYABO-2,5-DIHYDROFURAN GROUPS |
| WO2010142864A1 (en) * | 2009-06-09 | 2010-12-16 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | N-type organic semiconductors including at least two 2-dicyanomethylene-3-cyano-2,5-dihydrofuran groups |
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