CN102120814A - Soluble azafluorene conjugated polymer material as well as preparation and application thereof - Google Patents

Soluble azafluorene conjugated polymer material as well as preparation and application thereof Download PDF

Info

Publication number
CN102120814A
CN102120814A CN 201010590291 CN201010590291A CN102120814A CN 102120814 A CN102120814 A CN 102120814A CN 201010590291 CN201010590291 CN 201010590291 CN 201010590291 A CN201010590291 A CN 201010590291A CN 102120814 A CN102120814 A CN 102120814A
Authority
CN
China
Prior art keywords
conjugated polymer
diaza
polymer material
organic
fluorenes
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
Application number
CN 201010590291
Other languages
Chinese (zh)
Inventor
黄维
解令海
李伟杰
林进义
林宗琼
殷成蓉
赵剑锋
仪明东
陈琳
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nanjing Post and Telecommunication University
Nanjing University of Posts and Telecommunications
Original Assignee
Nanjing Post and Telecommunication University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nanjing Post and Telecommunication University filed Critical Nanjing Post and Telecommunication University
Priority to CN 201010590291 priority Critical patent/CN102120814A/en
Publication of CN102120814A publication Critical patent/CN102120814A/en
Pending legal-status Critical Current

Links

Images

Abstract

The invention provides a soluble azafluorene conjugated polymer material as well as preparation and application methods thereof, relating to the field of photoelectric materials and also relating to application of the soluble azafluorene conjugated polymer material to the fields of organic electroluminescence, organic solar cells, organic electricity storage, organic field effect transistors, biosensing, and the like. The soluble azafluorene conjugated polymer material has an alkyl 4,5-dizafluorene unit frame. A polymer I has the advantages that: (1) an alkyl 4, 5-dizafluorence unit has the characteristics of an electron acceptor; (2) a linear plane conformation is achieved, and the band gap is narrow; and (3) the polymer can be coordinated with metal ions. A semiconductor device prepared by utilizing the material provided by the invention achieves a satisfactory result; and the soluble azafluorene conjugated polymer material is about to serve as a photoelectric material with low cost and commercial potential.

Description

Solubility azepine fluorenes class conjugated polymer material and preparation and application
Technical field
The invention belongs to the photoelectric material technical field.Be specifically related to a class and contain special 4,5-diaza fluorene-based polymers material, and relate to of the application of such material in fields such as organic electroluminescent, organic field-effect tube, organic solar batteries, nonlinear optics, bio-sensing, organic optical storage and organic lasers.
Technical background
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.Nature 1990,347,539.] delivered respectively make film-type organic electroluminescence device (Organic Light-emitting Diodes) and polymer LED (PolymericLight-emitting Diodes) with organic and polymer fluorescent material since, 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, organic optical storage, nonlinear optics, bio-sensing and organic 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 many domestic and international universities and the concern and the input of research institution and company with practicality.Up to the present, high stability carrier transmission material of development of new and luminescent material become and improve organic electronic, photon, electric light and photoelectric device efficient and life-span key factor.
Up to the present, contain 4, the organic photoelectrical material of 5-diaza fluorene structural units also has high thermostability and high second-order transition temperature when showing good optical and electrical properties, therefore becomes a class practical organic optoelectronic material likely.Therefore, a large amount of articles and patent have been formed.Yet with 4,9 polymer-based material of introducing alkyl chain and forming do not have patent report on the 5-diaza fluorene structural units.4, the fluorene structured base polymer semiconductor material of 5-diaza shows following advantage: (1) is synthetic conveniently to be easy to get, and prepares a series of homopolymer and multipolymer; (2) has the linear plane conformation; (3) advantage such as high thermostability and second-order transition temperature.Therefore, the present invention has developed a series of 4 by simple synthetic route, and 5-diaza fluorenes class material has been introduced simultaneously and had the solubleness of increasing alkyl chain and enlarge such material in organic electronic, photoelectron, photon or photoelectric material use range.
Summary of the invention
Technical problem: the object of the present invention is to provide a kind of 4, fluorene structured polymer photoelectric material of 5-diaza and methods for making and using same thereof, design 4,5-diaza fluorenes monomer prepares relevant photoelectric functional material.In addition, pointed out of the application of such material in organic electronic fields such as organic electroluminescent, organic field-effect tube, organic optical storage and organic lasers.
Technical scheme: solubility azepine fluorenes class conjugated polymer material of the present invention is that alkyl replaces 4, and the unitary conjugated polymer photoelectric material of 5-diaza fluorenes has following general structure:
Figure BSA00000387121400021
Polymkeric substance I
In the formula: x is the numeral in 1～10, and y is the numeral in 0～10, and n is the numeral in 1～300.
R 1, R 2Identical or different during appearance, and be hydrogen; Or having straight chain, side chain or a cyclic alkyl chain of 1 to 22 carbon atom, one or more non-conterminous carbon atom can be by-NR 3-,-O-,-S-,-CO-O-,-CO-NR 3-displacement, perhaps one or more hydrogen atom is replaced by fluorine;
R 3, R 4For identical or different, and be H or straight chain, ring-type or collateralization alkyl, alkoxyl group, alkane sulfydryl or ester group with 1 to 22 carbon atom;
Identical or different when Ar occurs, and be a kind of in the following structure:
Figure BSA00000387121400022
In the described polymkeric substance I material, R 1, R 2Be selected from a kind of in hydrogen or normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl or positive certain herbaceous plants with big flowers base or the n-octyloxy chain respectively.
In the described polymkeric substance I material, get x, y all equal 1 and Ar get fluorenes, R simultaneously 1, R 2, R 3, R 4All be n-octyl, then constitute the following alkyl of molecular structure and replace 4, the unitary conjugated polymer photoelectric material of 5-diaza fluorenes:
In polymkeric substance I, when y equals zero, it is as follows then to constitute compound structure:
Figure BSA00000387121400032
The preparation method of solubility azepine fluorenes class conjugated polymer material comprises; The reaction conditions of Suzuki coupling (Suzuki) is triphenyl phosphorus palladium (Pd (PPh 3) 4)/salt of wormwood (K 2CO 3)/toluene/cesium fluoride (CsF)/triphenyl phosphorus (Ph 3P)/1,2-glycol dimethyl ether; Yamamoto (Yamamoto) link coupled reaction conditions is two (1, the 5-cyclooctadiene) nickels (COD) 2/ dipyridyl (bpy)/1, and the 5-cyclooctadiene (1,5-cyclooctadiene)/N, dinethylformamide (DMF);
4,5-diaza fluorenes monomer synthetic route is as follows:
Figure BSA00000387121400033
Wherein,
Step (1) is the bromination reaction that carries out under the condition of n-propylcarbinyl chloride/sulfur subchloride/pyridine/liquid bromine;
Step (2) is the oxidizing reaction of carrying out under the condition of the vitriol oil/nitric acid;
Step (3) is the reduction reaction under the condition of hydrazine hydrate;
Step (4) is carried out alkylated reaction under the bromooctane effect.
4, the preparation of 5-diaza fluorene-based polymers photoelectric material, Suzuki condensation polymerization reaction method is as follows:
Figure BSA00000387121400041
Method (2) is the Stille linked reaction: reactant is dihalide and/or two stannates and single stannate and/or single halogenide herein, perhaps corresponding single halogenide-single stannate derivatives monomer, linked reaction under alkaline condition and under the condition of palladium catalyst and solvent existence;
Method (3) is the Yamamoto linked reaction, and its reaction conditions is Ni (COD) 2/ bpy/1,5-cyclooctadiene/DMF.
For example, 4, the copolymer reaction that 5-diaza fluorenes class monomer and fluorenes monomer form is as follows:
Figure BSA00000387121400042
4,5-diaza fluorene-based polymers photoelectric material is as the LED device material, wherein the structure of LED device is transparent anode/hole injection layer/hole transmission layer/electronic barrier layer/luminescent layer/electron transfer layer/electron injecting layer/negative electrode, wherein, employing contains 4,5-diaza fluorene-based polymers semiconductor material is as hole transmission layer or luminescent layer, perhaps as the material of main part of luminescent layer.
Beneficial effect: characterized oligomer and high polymer material structure, the thermostability of having tested material by thermogravimetric analysis and differential thermal analysis by ultimate analysis, infrared spectra (FTIR), nucleus magnetic resonance (NMR), chromaticness online (GCMS), ground substance assistant laser parsing time-of-fight mass spectrometry (MALDI-TOF-MS), gel chromatography (GPC).
The wherein thermogravimetric analysis of such material and differential thermal analysis test has shown good thermostability.Therefore, the device of such material composition can effectively be eliminated defect problems such as crystallization and pin hole.Promise to be good hole mobile material, material of main part and red light material efficiently.
Such polymer materials also can be applied to the organic electronic fields such as organic semiconductor layer, solar-energy photo-voltaic cell, organic optical storage, organic laser material and organic non linear optical material in the field effect transistor.Polymer materials I is suitable for and makes plastic electronic material, photoelectron material; The device in plastic electronic field or element comprise polymkeric substance and organic light emitting diode device, organic solar batteries, organic laser diode component, organic field-effect tube, OTFT, organic integration circuit, bio-sensing device, organic optical storage, nonlinear optical element etc.; Use transport material, interface injecting material, conductive material, the photoelectric material that comprises as luminescent material and hole as organic electronic material.
In addition, on this basis, the various influences that preliminary device is estimated the end-blocking material have been designed to the behavior of device light emission.Device during at the luminescent properties of the injection of current carrier and transmission performance, material and as white light and phosphorescent light body material Subjective and Objective transmission ofenergy behavior and light amplification behavior design and study.Transparent anode is produced on on glass or the plastic, the triarylamine class hole mobile material of vacuum evaporation termination process of the present invention on conductive layer then, evaporation or spin coating luminescent layer or doped body material, evaporation one deck electron transfer layer, evaporation negative electrode at last again.Polymer materials I is as OLED and PLED device material, wherein the structure of electroluminescent device is transparent anode/hole injection layer/hole transmission layer/electronic barrier layer/luminescent layer hole blocking layer/electron transfer layer/electron injecting layer/negative electrode, wherein exist, perhaps as the device of the material of main part of the material of main part of white light and phosphorescence as hole transmission layer or electronic barrier layer.
Description of drawings
Fig. 1 .2,7-two bromo-4,5-diaza fluorenes 1H NMR spectrogram;
Fig. 2 .2,7-two bromo-9,9-dioctyl-4,5-diaza fluorenes 1H NMR spectrogram;
Fig. 3. poly-{ (9,9-dioctyl-4,5-diaza-2,7-two bases)-copolymerization-(9,9-dioctyl fluorene-2,7-two bases) } 1H NMR spectrogram;
Embodiment
Understand the content of patent of the present invention better, further specify technical scheme of the present invention below by concrete example and legend, specifically comprise synthetic, property testing and device preparation.But these embodiments do not limit the present invention.
Embodiment 1, poly-(9,9-dioctyl-4,5-diaza fluorenes) homopolymer material preparation:
3,8-two bromo-1,10-phenanthroline
With 5.41g 1,10-phenanthroline, 200mL n-propylcarbinyl chloride, 7.3mL sulfur subchloride, 7.3mL pyridine, 4.5mL the liquid bromine is mixed in the 250mL round-bottomed flask, the 17h that refluxes under 90 ℃ the condition, cooling, suction filtration, filter cake is used dichloromethane extraction, the organic layer anhydrous magnesium sulfate drying after using the 100mL distilled water wash, revolve to steam to remove and desolvate, silicagel column separates, sherwood oil: ethyl acetate=6: 1 (v: v) make eluent, obtain white solid.Use the sym.-tetrachloroethane recrystallization again, obtain the 4.05g white needle-like crystals.Productive rate: 40%.
GC-MS(EI-m/z)：338(M +)。
2,7-two bromo-4,5-diaza Fluorenone
In the 250mL round-bottomed flask, add 5.26g 3 successively, 8-two bromo-1, the 10-phenanthroline, 2.26g KBr adds dense H again 2SO 4And HNO 3Mixing solutions, be warming up to 100 ℃, the reaction 5h.After being cooled to room temperature, it is yellow that reaction solution is.Pour in the water under stirring, water layer becomes yellow and precipitation occurs, regulates PH to alkalescence, and this moment, solution and sedimentary color deepened gradually to blackish green.Suction filtration, the filter cake washed with dichloromethane, the organic layer anhydrous magnesium sulfate drying revolves and desolventizes, and promptly obtains the faint yellow product of 2.11g.Productive rate: 40%.
GC-MS(EI-m/z)：340(M +)。
2,7-two bromo-4,5-diaza fluorenes
In the 50mL round-bottomed flask, add 3.4g 2,7-two bromo-4,5-diaza Fluorenone and 12mL hydrazine hydrate are warming up to 180 ℃ under stirring, reaction 6h.After being cooled to room temperature, dichloromethane extraction, wash 3 times after, anhydrous MgSO 4Drying, suction filtration screws out solvent, obtains the 2.61g faint yellow solid.Productive rate: 80%.
GC-MS(EI-m/z)：326(M +)。
2,7-two bromo-9,9-dioctyl-4,5-diaza fluorenes
In the 50mL round-bottomed flask, add 0.33g 2 successively, 7-two bromo-4,5-diaza fluorenes, the anhydrous THF of 20mL, the 0.9g potassium tert.-butoxide behind the stirring 30min, adds the 0.5g n-octane bromide, stirs under the room temperature and spends the night.Dichloromethane extraction, distilled water wash 3 times, organic layer anhydrous magnesium sulfate drying.Silicagel column separates, and eluent is a sherwood oil: ethyl acetate=4: 1 (v: v), obtain the 0.17g white solid.Productive rate: 31%.
GC-MS(EI-m/z)：550(M +)。
The preparation of poly-(9,9-dioctyl-4,5-diaza fluorenes) material:
Solvent for use must be removed air before use.
Under the atmosphere of lucifuge and high-purity argon gas, in the 50mL round-bottomed flask, add dipyridyl (2.6eq) successively, Ni (COD) 2(2.6eq), behind the COD (10eq), extraction gas three times, inject 10mL toluene, be heated to 70 ℃ and keep 30min.With 2,7-two bromo-9,9-dioctyl-4 after 5-diaza fluorenes (1.0equiv.) is dissolved in toluene solution, is injected in the 50mL reaction flask.Be warming up to 80 ℃, stir 48h, cooling is also poured whole mixture in the methyl alcohol into.Filtration is also removed oligomer and small molecules and residual catalyzer with Soxhlet tubular type extraction plant extracting solid precipitation 48h in acetone.Obtain white solid.Productive rate: 60%.
GPC：M n＝15560；PDI＝2.0。
Embodiment 2,9,9-dioctyl-4, and 5-diaza fluorenes and 9,9-dioctyl fluorene copolymer material:
9,9-dioctyl-2,7-two (4,4,5,5-tetramethyl--[1,3,2] dioxo bora pentamethylene base) fluorenes at first, get 9,9-dioctyl-2,7-dibromo fluorenes (1.0equiv.) are put into 250ml two neck flasks, described flask has carried out heat drying and has vacuumized logical nitrogen airtight back three times, uses through strict anhydrous and oxygen-free device processing before high pure nitrogen uses.Then, reaction unit is put into-78 ℃ the low temperature that is produced by dry ice and acetone bathe, and get the fresh distillatory tetrahydrofuran (THF) (20ml) of anhydrous and oxygen-free.Subsequently n-Butyl Lithium (3.0equiv.) slowly is added in the two neck flasks, and under-78 ℃ low temperature, reacted about 1 hour, last, with 2-isopropoxy-4,4,5,5-tetramethyl--1,3,2-dioxy borine (3.0equiv.) is injected into reactor rapidly, slowly rises to room temperature, and reaction is spent the night.Reaction finishes with frozen water cancellation reaction, sodium-chlor washing extracted with diethyl ether, drying, the dried solvent of vacuum rotary steam, obtains thick product.Recrystallization is purified in normal hexane/toluene mixed solvent, obtains white solid (productive rate is 93%).
9,9-dioctyl-4,5-diaza fluorenes and 9, the preparation of 9-dioctyl fluorene copolymer material
Careful purifying monomer 9,9-dioctyl-2,7-two (4,4,5,5-tetramethyl--[1,3,2] dioxo bora pentamethylene base) fluorenes and monomer 2,7-two bromo-9,9-dioctyl-4 is behind the 5-diaza fluorenes, 1: 1 in molar ratio feed ratio mixed dissolution adds catalyzer (PPh under the atmosphere of high-purity argon gas in toluene solution 3) 4Pd (0) (0.5-2.0mol%) and drips several Aliquat 336, adds 2M Na simultaneously 2CO 3The aqueous solution.Be reflected under the vigorous stirring and refluxed 3 days.After reaction finished, cooling was also poured whole mixture in the methyl alcohol into.Filtration is also removed oligomer and small molecules and residual catalyzer with Soxhlet tubular type extraction plant extracting solid precipitation 48h in acetone.Obtain white solid (productive rate: 76%).
GPC：M n＝7212；PDI＝2.5。
Embodiment 3, to the hot assay determination of poly-{ (9,9-dioctyl-4,5-diaza-2,7-two bases)-copolymerization-(9,9-dioctyl fluorene-2,7-two bases) } material:
Thermogravimetric analysis (TGA)) carry out on the DTG-60H of Tianjin, island company (Shimadzu) thermogravimetric analyzer, the heating sweep velocity is that 10 ℃/min and nitrogen flow rate are 20cm 3/ min.Differential scanning calorimetry (DSC) carries out on the DSC-60A of Tianjin, island company (Shimadzu) tester, and sample at first is heated to the state of low ten degree of decomposed sample temperature with the speed of 10 ℃/min, and then, beginning is got back in cooling under the liquid nitrogen condition
Temperature, the same second time is with the speed heat temperature raising scanning of 10 ℃/min.The heat decomposition temperature of poly-{ (9,9-dioctyl-4,5-diaza-2,7-two bases)-copolymerization-(9,9-dioctyl fluorene-2,7-two bases) } material is greater than 350 ℃.
Embodiment 4, to poly-{ (9,9-dioctyl-4,5-diaza-2,7-two bases)-copolymerization-(9,9-dioctyl fluorene-2,7-two bases) } preparation as the electroluminescent device of luminescent material:
One with poly-{ (9,9-dioctyl-4,5-diaza-2,7-two bases)-copolymerization-(9,9-dioctyl fluorene-2,7-two bases) } as the single layer device of luminescent layer, promptly device architecture be ITO/ poly-(9,9-dioctyl-4,5-diaza-2,7-two bases)-copolymerization-(9,9-dioctyl fluorene-2,7-two bases) } (20nm)/LiF
Figure BSA00000387121400071
/ Al,, wherein ITO is the transparency electrode of square resistance 10-20 Ω/; Poly-{ (9,9-dioctyl-4,5-diaza-2,7-two bases)-copolymerization-(9,9-dioctyl fluorene-2,7-two bases) } adopt spin coating technique, and film thickness is 10～200nm; Evaporation LiF buffer layer again, evaporation rate
Figure BSA00000387121400072
At last, AM aluminum metallization negative electrode.

Claims (6)

1. a solubility azepine fluorenes class conjugated polymer material is characterized in that this material is that alkyl replaces 4, and the unitary conjugated polymer photoelectric material of 5-diaza fluorenes has following polymkeric substance I general structure:
Figure FSA00000387121300011
Polymkeric substance I
In the formula: x is the numeral in 1～10, and y is the numeral in 0～10, and n is the numeral in 1～300;
R 1, R 2Identical or different during appearance, and be hydrogen or straight chain, side chain or the cyclic alkyl chain with 1 to 22 carbon atom, one or more non-conterminous carbon atom can be by-NR 3-,-O-,-S-,-CO-O-,-CO-NR 3-displacement, perhaps one or more hydrogen atom is replaced by fluorine;
R 3, R 4For identical or different, and be H or straight chain, ring-type or collateralization alkyl, alkoxyl group, alkane sulfydryl or ester group with 1 to 22 carbon atom;
Identical or different when Ar occurs, and be a kind of in the following structure:
Figure FSA00000387121300012
2. solubility azepine fluorenes class conjugated polymer material according to claim 1 is characterized in that in the described polymkeric substance I material R 1, R 2Be selected from a kind of in hydrogen or normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl or positive certain herbaceous plants with big flowers base or the n-octyloxy chain respectively.
3. alkyl according to claim 1 replaces 4, and 5-diaza fluorene-based polymers photoelectric material is characterized in that in the described polymkeric substance I material, get x, y all equal 1 and Ar get fluorenes, R simultaneously 1, R 2, R 3, R 4All be n-octyl, it is as follows then to constitute molecular structure:
Figure FSA00000387121300013
4. the preparation method of a solubility azepine fluorenes class conjugated polymer material as claimed in claim 1 is characterized in that the preparation of this material comprises; The reaction conditions of Suzuki cross-coupling is triphenyl phosphorus palladium (Pd (PPh 3) 4)/salt of wormwood (K 2CO 3)/toluene/cesium fluoride (CsF)/triphenyl phosphorus (Ph 3P)/1,2-glycol dimethyl ether; The reaction conditions of Yamamoto cross-coupling is two (1, the 5-cyclooctadiene) nickels (COD) 2/ dipyridyl (bpy)/1,5-cyclooctadiene/N, dinethylformamide (DMF);
4,5-diaza fluorenes monomer synthetic route is as follows:
Wherein,
Step (1) is the bromination reaction that carries out under the condition of n-propylcarbinyl chloride/sulfur subchloride/pyridine/liquid bromine;
Step (2) is the oxidizing reaction of carrying out under the condition of the vitriol oil/nitric acid;
Step (3) is the reduction reaction under the condition of hydrazine hydrate;
Step (4) is carried out alkylated reaction under the bromooctane effect.
5. according to the preparation method of the described solubility azepine of claim 4 fluorenes class conjugated polymer material, it is characterized in that 4, the preparation of 5-diaza fluorene-based polymers photoelectric material, Suzuki cross-coupling condensation polymerization reaction method is as follows:
Figure FSA00000387121300022
6. the application of a solubility azepine fluorenes class conjugated polymer material as claimed in claim 1, it is characterized in that 4,5-diaza fluorene-based polymers photoelectric material is as the LED device material, wherein the structure of LED device is transparent anode/hole injection layer/hole transmission layer/electronic barrier layer/luminescent layer/electron transfer layer/electron injecting layer/negative electrode, wherein, employing contains 4,5-diaza fluorene-based polymers semiconductor material is as electron transfer layer or luminescent layer, perhaps as the material of main part of luminescent layer.
CN 201010590291 2010-12-13 2010-12-13 Soluble azafluorene conjugated polymer material as well as preparation and application thereof Pending CN102120814A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 201010590291 CN102120814A (en) 2010-12-13 2010-12-13 Soluble azafluorene conjugated polymer material as well as preparation and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 201010590291 CN102120814A (en) 2010-12-13 2010-12-13 Soluble azafluorene conjugated polymer material as well as preparation and application thereof

Publications (1)

Publication Number Publication Date
CN102120814A true CN102120814A (en) 2011-07-13

Family

ID=44249492

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 201010590291 Pending CN102120814A (en) 2010-12-13 2010-12-13 Soluble azafluorene conjugated polymer material as well as preparation and application thereof

Country Status (1)

Country Link
CN (1) CN102120814A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210097449A (en) * 2020-01-30 2021-08-09 (주)알로스 New polymer and organic electroluminescent device comprising the same
KR20210097496A (en) * 2020-01-30 2021-08-09 (주)알로스 New polymer and organic electroluminescent device comprising the same
CN115852507A (en) * 2023-03-04 2023-03-28 扬州恒诚织布有限公司 Anti-static fabric and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004091444A (en) * 2002-09-04 2004-03-25 Canon Inc Diazafluorene compound and organic light emitting element using the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004091444A (en) * 2002-09-04 2004-03-25 Canon Inc Diazafluorene compound and organic light emitting element using the same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210097449A (en) * 2020-01-30 2021-08-09 (주)알로스 New polymer and organic electroluminescent device comprising the same
KR20210097496A (en) * 2020-01-30 2021-08-09 (주)알로스 New polymer and organic electroluminescent device comprising the same
KR102299609B1 (en) 2020-01-30 2021-09-09 (주)알로스 New polymer and organic electroluminescent device comprising the same
KR102299614B1 (en) 2020-01-30 2021-09-09 (주)알로스 New polymer and organic electroluminescent device comprising the same
CN115852507A (en) * 2023-03-04 2023-03-28 扬州恒诚织布有限公司 Anti-static fabric and preparation method thereof

Similar Documents

Publication Publication Date Title
Rao et al. A 19.0% efficiency achieved in CuOx-based inverted CH3NH3PbI3− xClx solar cells by an effective Cl doping method
CN101139317B (en) Organic semiconductor material containing carbazole unit and synthesis
CN103224486B (en) S,S-dioxo-dibenzothiophene monomer containing polar substituent groups, water/alcohol soluble polymers thereof, and application thereof
CN104725613B (en) n-type water and alcohol soluble conjugated polymer material containing naphtho-diamide ring, and preparation method and application of material
CN101440082A (en) Spirofluorene xanthene material, and preparation and use thereof
CN100490206C (en) Organic/high molecular light emitting diode
CN101161698B (en) Break-in conjugated branched polymer material and preparation method and uses thereof
JP5425338B2 (en) Copolymer containing anthracene and pearselenol, its production method and its application
CN108864137B (en) Receptor compound, preparation method and application thereof, and photovoltaic cell containing receptor compound
CN101717396A (en) Triazine type photonic functional material and preparation and application method thereof
CN101397365B (en) 1,8-carbazoles polymer photovoltaic material, preparation and use method thereof
EP2530084B1 (en) Copolymer containing fluorenylporphyrin-anthracene, preparation method and use thereof
CN101492443B (en) Complex whorl aryl fluorene material, preparation and application method thereof
CN101492442A (en) Complex diaryl fluorene material, preparation and application method thereof
CN102120814A (en) Soluble azafluorene conjugated polymer material as well as preparation and application thereof
CN102134308A (en) Aza-fluorenone conjugated polymer photoelectric material and preparation and application methods thereof
WO2021203663A1 (en) Electroluminescent polymer based on phenanthroimidazole units, preparation method therefor, and use thereof
CN102807554B (en) Organic semiconductor material containing naphthalene, anthracene and dibenzothiophene sulfone unit, preparation method and application thereof
JP5665993B2 (en) Organic semiconductor material containing fluorene and preparation method thereof
CN100582129C (en) Rear modified polyvinyl carbazole material and preparation method and uses thereof
CN114349771B (en) Hexabenzocoronene-based non-fullerene acceptor material and preparation and application thereof
CN111187280A (en) Doping-free hole transport material based on indeno [1,2-b ] carbazole and synthetic method and application thereof
CN102807556B (en) Organic semiconductor material containing naphthalene, anthracene, dibenzothiophene sulfone units and preparation method and application thereof
CN105254466A (en) Pyrene organic material, preparing method and application of pyrene organic material
CN101503488B (en) Poly (diaryl fluorene ethylene) material, as well as preparation and use 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
C12 Rejection of a patent application after its publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20110713