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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- carbazole
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- 239000000463 material Substances 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000005829 trimerization reaction Methods 0.000 title claims description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title abstract description 15
- 150000003384 small molecules Chemical class 0.000 claims abstract description 27
- 150000001716 carbazoles Chemical class 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 229920001088 polycarbazole Polymers 0.000 claims description 3
- ZPXKSVJLJLHQMB-UHFFFAOYSA-N NC1=CC=CC=C1.C1(=CC=CC=C1)C1=CC=CC=C1.[N] Chemical compound NC1=CC=CC=C1.C1(=CC=CC=C1)C1=CC=CC=C1.[N] ZPXKSVJLJLHQMB-UHFFFAOYSA-N 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- -1 thiophene-2-yl Chemical group 0.000 claims description 2
- 230000005669 field effect Effects 0.000 abstract description 4
- 238000011160 research Methods 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract 1
- 230000021615 conjugation Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Abstract
本发明公开了一种新型的基于三聚咔唑类窄带隙共轭小分子材料及其制备方法。本发明基于三聚咔唑类窄带隙共轭小分子材料，结构如说明书附图中图1所示。目前，具有给受体结构的窄带隙共轭小分子是当前研究的热点，三聚咔唑分子具有非常好的平面性，较高的载流子迁移率，并可以作为很好的电子给体。基于三聚咔唑类共轭小分子材料在有机场效应管和有机发光二级管中的应用已经有了一些研究。本发明公开了一种新型的基于三聚咔唑类窄带隙共轭小分子材料，该材料具有很好的溶解性以及较宽的紫外吸收，本发明基于三聚咔唑类窄带隙共轭小分子材料可用作聚合物太阳能电池的给体材料、有机场效应晶体管的n-型半导体材料和有机光导体的给体材料等。
The invention discloses a novel trimeric carbazole-based narrow bandgap conjugated small molecule material and a preparation method thereof. The present invention is based on trimeric carbazole narrow-bandgap conjugated small molecule materials, the structure of which is shown in Figure 1 in the accompanying drawings. At present, the narrow bandgap conjugated small molecules with donor-acceptor structures are the current research hotspots. Trimeric carbazole molecules have very good planarity, high carrier mobility, and can be used as good electron donors. . There have been some studies on the application of trimeric carbazole-based conjugated small molecule materials in organic field effect transistors and organic light-emitting diodes. The invention discloses a novel trimeric carbazole-based narrow-bandgap conjugated small molecule material, which has good solubility and wide ultraviolet absorption. The invention is based on trimeric carbazole-based narrow-bandgap conjugated Molecular materials can be used as donor materials for polymer solar cells, n-type semiconductor materials for organic field effect transistors, and donor materials for organic photoconductors.
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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| CN201210322617.6A CN103664950A (en) | 2012-09-04 | 2012-09-04 | Novel trimerization carbazole based narrow band gap conjugated micromolecule material and preparation method thereof |
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Cited By (5)
| 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 |
| US12108666B2 (en) | 2018-09-26 | 2024-10-01 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
-
2012
- 2012-09-04 CN CN201210322617.6A patent/CN103664950A/en active Pending
Cited By (10)
| 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 |
| US12108666B2 (en) | 2018-09-26 | 2024-10-01 | Idemitsu Kosan Co., Ltd. | Compound and organic electroluminescence device |
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Application publication date: 20140326 |
