CN103664950A - Novel trimerization carbazole based narrow band gap conjugated micromolecule material and preparation method thereof - Google Patents
Novel trimerization carbazole based narrow band gap conjugated micromolecule material and preparation method thereof Download PDFInfo
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- CN103664950A CN103664950A CN201210322617.6A CN201210322617A CN103664950A CN 103664950 A CN103664950 A CN 103664950A CN 201210322617 A CN201210322617 A CN 201210322617A CN 103664950 A CN103664950 A CN 103664950A
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- trimerization
- band gap
- narrow band
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Abstract
The invention discloses a novel trimerization carbazole based narrow band gap conjugated micromolecule material and a preparation method thereof. The structure of the trimerization carbazole based narrow band gap conjugated micromolecule material disclosed by the invention is as shown in a figure 1 in the description drawings. At present, a narrow band gap conjugated micromolecule material with a donor-acceptor structure is a hot point in present research, and trimerization carbazole molecules have good planarity and high carrier mobility and can be good electronic donors. The application of the trimerization carbazole based narrow band gap conjugated micromolecule material in organic field effect transistors and organic light emitting diodes is already studied at present. The invention discloses the novel trimerization carbazole based narrow band gap conjugated micromolecule material which has good solubility and wide ultraviolet absorption, the trimerization carbazole based narrow band gap conjugated micromolecule material can be used as a donor mateiral of a polymer solar battery, an n-type semiconductor material of the organic field effect transistors, a donor material of an organic light conductor, and the like.
Description
Technical field
The invention belongs to organic photovoltaic cell Material Field, particularly a kind of novel based on narrowband gap conjugated small molecule material of trimerization carbazoles and preparation method thereof.In the situation that the whole world is faced with energy dilemma, photoelectric conversion technique is considered to one of most important renewable energy source.Wherein, organic photovoltaic cell has cheapness, light weight, the advantage can big area prepared received widely and paid close attention to.One of important factor that obtains high-photoelectric transformation efficiency is the electron donor material of exploitation excellent performance.At present, the highest efficiency of conversion has reached 10%.
Background technology
The application of conjugation small molecules in organic solar batteries is also a very important research direction.It is accurate that conjugation small molecules has structure, and the advantages such as easy purifying and molecular structure variation have important application in organic solar batteries.In addition, due to the exact controllability of structure, the impact that small molecules can reduce batch to greatest extent, also can be used as the relation that Model Molecule is furtherd investigate molecular structure and performance.From the angle of device manufacture method, conjugation small molecules can be categorized as evaporation processed-type small molecules and solution processable type small molecules.For the method for evaporation, solution method processing is simpler and easy, and save energy, is easily applied to industrial production.At present, can use the small molecules of solution method processing device more and more, demonstrate its good performance, highest energy efficiency of conversion has arrived 6.7%, and this numerical value can compare favourably with polymer materials.
The Specifeca tion speeification of organic solar batteries comprises photoelectric transformation efficiency (PCE, η), open circuit photovoltage (Voc), short-circuit photocurrent (Isc)/short-circuit photocurrent density (Jsc), packing factor (FF), the life-span of incident photon-electronic switch efficiency (IPCE) and battery etc.The height of open circuit voltage is closely related with the highest not occupied orbital (HOMO) energy level, and HOMO energy level is lower, and open circuit voltage is higher.Short-circuit current depends on the effective absorption of material to sunlight, and exciton is in effective separation and electric charge transmission fast in two-phase of material two-phase interface.Through further investigation for many years, people have formed some common recognitions in the mentality of designing of material, are summarized as follows: (1) has lower energy gap (optimum value is probably at 1.5eV), thereby effectively absorb sunlight, is converted into short-circuit current; (2) thus having suitable HOMO and lumo energy obtains compared with high open circuit voltage and less of the poor loss of avoiding energy of acceptor lumo energy; (3) good solvability and be beneficial to solution method processing and can form the pattern that nanoscale is optimized with the consistency of fullerene derivate.Thinking based on above, the organic materials of plurality of narrow band gap is designed to be synthesized and to be applied in organic solar batteries.
The invention discloses a kind of novel based on narrowband gap conjugated small molecule material of trimerization carbazoles and preparation method thereof.The present invention is based on the narrowband gap conjugated small molecule material of trimerization carbazoles, structure is suc as formula shown in I.At present, the narrowband gap conjugated small molecules having to receptor structure is the focus of current research, and three polycarbazole molecules have extraordinary planarity, higher carrier mobility, and can be used as good electron donor(ED).Application based on trimerization carbazoles conjugation small molecule material in organic field-effect tube and organic light emitting diode has had some researchs.The invention discloses a kind of novel based on the narrowband gap conjugated small molecule material of trimerization carbazoles, this has good solvability and wider uv-absorbing, the present invention is based on the narrowband gap conjugated small molecule material of trimerization carbazoles and can be used as the donor material of polymer solar battery, the n-N-type semiconductorN material of organic field effect tube and the donor material of organic photoconductor etc.
Summary of the invention
The present invention is intended to a kind of novel based on narrowband gap conjugated small molecule material of trimerization carbazoles and preparation method thereof
In the present invention, the preparation method of TCZTBT is as follows:
TCZTBT synthetic route
Specifically, the preparation method of TCZTBT in the present invention, its key step is:
Under nitrogen atmosphere, take toluene and water as solvent, by 4-(5-(4-(5-bromothiophene-2-yl)-[1,2,5] diazosulfide-7-yl) thiophene-2-yl)-nitrogen, nitrogen-phenylbenzene aniline and 2,6,10-tri-(4,4,5,5-tetramethyl--1,3,2-dioxa borine-2-yl)-nitrogen-tri-(hexyl) three polycarbazoles, mol ratio is 3: 1, under tetrakis triphenylphosphine palladium catalysis, at 100-120 ℃ of temperature, reacts 5 days, obtains TCZTBT structure based on the narrowband gap conjugated small molecule material of trimerization carbazoles
embodiment
Embodiment 1: preparation TCZTBT structure based on the narrowband gap conjugated small molecule material 70.0mg of trimerization carbazoles monomer M 1,200.0mg M2,20mL toluene, 3mL water, 4.61mg Tetrabutyl amonium bromide and 1.97g K
2cO
3mixture in the pipe valve flask of 100ML, adding 12.43mg Pd (PPh
3)
4before, all through repeatedly filling denitrogenation gas, then system stirring and refluxing under nitrogen atmosphere is reacted 5 days.Then cooling system, adds water and methylene dichloride; With separating funnel, separate organic layer and wash organic phase with water three times.Then organic phase column chromatography for separation.Finally under high vacuum, be dried and obtain 120.2mg scarlet polymkeric substance TCZTBT, productive rate is 75.28%.
Accompanying drawing explanation
Fig. 1 is based on the narrowband gap conjugated small molecule material TCZTBT of trimerization carbazoles chemical structural drawing;
Fig. 2 is at solution and film medium ultraviolet visible absorption spectra figure based on the narrowband gap conjugated small molecule material TCZTBT of trimerization carbazoles.
Claims (2)
- One kind novel based on narrowband gap conjugated small molecule material of trimerization carbazoles and preparation method thereof.
- 2. the method for material described in claim 1, key step is:Under nitrogen atmosphere, take toluene and water as solvent, by 4-(5-(4-(5-bromothiophene-2-yl)-[1,2,5] diazosulfide-7-yl) thiophene-2-yl)-nitrogen, nitrogen-phenylbenzene aniline and 2,6,10-tri-(4,4,5,5-tetramethyl--1,3,2-dioxa borine-2-yl)-nitrogen-tri-(hexyl) three polycarbazoles, mol ratio is 3: 1, under tetrakis triphenylphosphine palladium catalysis, at 100-120 ℃ of temperature, reacts 5 days, obtains formula TCZTBT structure based on the narrowband gap conjugated small molecule material of trimerization carbazoles.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107033150A (en) * | 2017-04-26 | 2017-08-11 | 南京邮电大学 | One kind three and the trapezoidal organic semiconductor laser material of carbazyl and preparation method and application |
| CN108794494A (en) * | 2018-06-18 | 2018-11-13 | 南京邮电大学 | One kind three and carbazole-aromatic amine derivant hole mobile material and the preparation method and application thereof |
| CN108948026A (en) * | 2018-06-15 | 2018-12-07 | 南京邮电大学 | One kind three and carbazole-phenyl hole mobile material and the preparation method and application thereof |
| US10658594B2 (en) | 2017-12-06 | 2020-05-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
-
2012
- 2012-09-04 CN CN201210322617.6A patent/CN103664950A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107033150A (en) * | 2017-04-26 | 2017-08-11 | 南京邮电大学 | One kind three and the trapezoidal organic semiconductor laser material of carbazyl and preparation method and application |
| CN107033150B (en) * | 2017-04-26 | 2019-03-08 | 南京邮电大学 | One kind three and the trapezoidal organic semiconductor laser material of carbazyl and the preparation method and application thereof |
| US10658594B2 (en) | 2017-12-06 | 2020-05-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10672989B2 (en) | 2017-12-06 | 2020-06-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US10680181B2 (en) | 2017-12-06 | 2020-06-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US11557730B2 (en) | 2017-12-06 | 2023-01-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| US11569449B2 (en) | 2017-12-06 | 2023-01-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and novel compound |
| CN108948026A (en) * | 2018-06-15 | 2018-12-07 | 南京邮电大学 | One kind three and carbazole-phenyl hole mobile material and the preparation method and application thereof |
| CN108794494A (en) * | 2018-06-18 | 2018-11-13 | 南京邮电大学 | One kind three and carbazole-aromatic amine derivant hole mobile material and the preparation method and application thereof |
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Application publication date: 20140326 |