CN108623613A - A kind of preparation method and application of nitrogenous, sulphur fused ring compound - Google Patents

A kind of preparation method and application of nitrogenous, sulphur fused ring compound Download PDF

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Publication number
CN108623613A
CN108623613A CN201810372779.8A CN201810372779A CN108623613A CN 108623613 A CN108623613 A CN 108623613A CN 201810372779 A CN201810372779 A CN 201810372779A CN 108623613 A CN108623613 A CN 108623613A
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phenyl
compound
epoxide
mol
solution
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刘颖
高腾
吉元昭
吴彦超
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Harbin Institute of Technology Weihai
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Harbin Institute of Technology Weihai
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons

Abstract

The present invention provides a kind of preparation method and applications of nitrogenous, sulphur fused ring compound.Synthetic method of the present invention is high with yield, the time is short, simple operation and other advantages, and using the reagent of conventional low cost, reduces the cost of preparation, application easy to spread.It can be applied in fields such as organic electroluminescent, organic field-effect tube, organic second-order non-linear, chiral liquid crystal and biological medicines based on nitrogenous, sulphur fused ring compound.

Description

A kind of preparation method and application of nitrogenous, sulphur fused ring compound
Technical field
The present invention relates to a kind of preparation method and applications of nitrogenous, sulphur fused ring compound.
Background technology
Novel pi-conjugated organic semi-conductor design and synthesis have attracted the concern of more and more researchers, because it Have potential application value in various photoelectric devices.Especially linearly condense and ring class molecule can be applied to Organic field effect tube（OFETs）, light emitting diode（LEDs）And photovoltaic cell（Referring to Anthony, J. E. Chem. Rev. 2006, 106, 5028.）.Research interest in recent years focuses primarily upon pentacene and its derivative.Existing research table It is bright（Referring to Lin, Y.-Y.; Gundlach, D. J.; Nelson, S. F.; Jackson, T. N. IEEE Electron Device Lett. 1997, 18, 606.）Its SiO in chemical modification2OFET made of/Si substrate depositions Device shows that outstanding charge carrier mobility is 1.5 cm2/(V·s).But there is permitted when pentacene is applied to device More defects, such as poor solubility, in air limited stability and the accumulation unfavorable in solid-state（Referring to Sheraw, C. D.; Jackson, T. N.; Eaton, D. L.; Anthony, J. E. Adv. Mater. 2003,15, 2009.）, Overcome a strategy of these defects be in condensed ring system introducing hetero-atoms come construct more stablize trapezoidal condensed molecule. Sulphur shows various intermolecular interactions as the introducing of thiophene-structure, such as Van der Waals force, pi-pi accumulation and sulphur- Sulphur interacts, these all play a role to obtaining high mobility（Referring to Lemaur, V.; da Silva Filho, D. A.; Coropceanu, V.; Lehmann, M.; Geerts, Y.;Piris, J.; Debije, M. G.; van de Craats, A. M.; Senthilkumar, K.; Siebbeles, L.D. A.; Warman, J. M.; Brédas, J.-L.; Cornil, J. J. Am. Chem. Soc. 2004, 126,3271.）.In addition, nitrogen-atoms Introducing can be good at the stability of reinforcing material.Therefore, we, which design, has synthesized two nitrogenous, sulphur seriations simultaneously Close object, it is desirable to which the mobility and stability of material can be increased.
Invention content
Present invention aims at provide a kind of preparation method and application of nitrogenous, sulphur fused ring compound.For existing skill The deficiency of art, the present invention is intended to provide a kind of preparation method of nitrogenous, sulphur fused ring compound, condensed conjugation material prepared therefrom Material has excellent solubility property and carrier transmission performance, is dissolved in organic solvent, is then coated in ito glass, silicon On the substrates such as piece or ceramics, soft, high-sequential transparent membrane can be formed after heating anneal appropriate processing；Simultaneously Big pi-conjugated structure is conducive to carrier transport, therefore the present invention also provides a kind of this nitrogenous, sulphur fused ring compounds organic Application in field of thin film transistors.
Description of the drawings
Fig. 1 is a kind of structure chart of nitrogenous, sulphur fused ring compound；
Fig. 2 is reaction synthetic route general formula figure；
Fig. 3 is the synthetic route chart of compound 3；
Fig. 4 is the synthetic route chart of compound 6；
Fig. 5 is the synthetic route chart of compound 9；
Fig. 6 is the synthetic route chart of compound 12；
Fig. 7 is the synthetic route chart of compound 15；
Fig. 8 is the synthetic route chart of compound 18.
Specific implementation mode
Its reaction process is as shown in Figure 2.
Embodiment 1：
Compound 3（Fig. 1-b）Specific preparation method it is as follows, synthesis equation be Fig. 3：
（1）At room temperature, by compound 1（1.00-1.50 mol/L）、S8（0.50-1.00 mol/Ls）It is dissolved in N, N- bis- In methylformamide and triethylamine solution, reacts 3-4 days, obtain compound 2；
（2）In 110 DEG C -115 DEG C, oxygen atmosphere, by compound 2（1.00-1.05 mol/L）, cyclohexanone analog compound （5.50-6.00 mol/L）, palladium trifluoroacetate (7.00-9.00% mol/Ls), (7.00-9.00%'s diamino-pyridine rubs You/liter), citric acid（0.40-0.60 mol/Ls）It is dissolved in toluene solution, 17h-19h is reacted, obtains compound 3.Nuclear-magnetism is total The hydrogen that shakes is composed1H NMR (400 MHz, CDCl3) d 8.05 (m, 1H),7.68 (m, 1H),7.61 (m, 1H),7.48(m, 1H),7.43 (m, 1H),7.32 (m, 1H),7.22 (m, 1H);Carbon-13 nmr spectra13C NMR (100 MHz, CDCl3) δ 150.4, 147.3, 141.4, 138.0, 129.9, 129.3, 129.0 , 128.3, 127.4, 127.0, 122.6, 118.7。
Embodiment 2：
Compound 6（Fig. 1-c）Specific preparation method it is as follows, synthesis equation be Fig. 4：
（1）At room temperature, by compound 4（1.00-1.50 mol/L）、S8（0.50-1.00 mol/Ls）It is dissolved in N, N- bis- In methylformamide and triethylamine solution, reacts 3-4 days, obtain compound 5；
（2）In 110 DEG C -115 DEG C, oxygen atmosphere, by compound 5（1.00-1.05 mol/L）, cyclohexanone analog compound （5.50-6.00 mol/L）, palladium trifluoroacetate (7.00-9.00% mol/Ls), (7.00-9.00%'s diamino-pyridine rubs You/liter), citric acid（0.40-0.60 mol/Ls）It is dissolved in toluene solution, 17h-19h is reacted, obtains compound 6.Nuclear-magnetism is total The hydrogen that shakes is composed1H NMR (400 MHz, CDCl3) d 8.68 (m, 1H),7.89 (m, 1H),7.73(m, 1H),7.67 (m, 1H),7.60(m, 1H),7.54 (m, 1H),7.32 (m, 1H);Carbon-13 nmr spectra13C NMR (100 MHz, CDCl3) δ 154, 151.5, 149.8, 135.7, 134.3, 128.6,128.1, 126.27, 126.2 ,125.7, 124.1, 120.8。
Embodiment 3：
Compound 9（Fig. 1-d）Specific preparation method it is as follows, synthesis equation be Fig. 5：
（1）At room temperature, by compound 7（1.00-1.50 mol/L）、S8（0.50-1.00 mol/Ls）It is dissolved in N, N- bis- In methylformamide and triethylamine solution, reacts 3-4 days, obtain compound 8；
（2）In 110 DEG C -115 DEG C, oxygen atmosphere, by compound 8（1.00-1.05 mol/L）, cyclohexanone analog compound （5.50-6.00 mol/L）, palladium trifluoroacetate (7.00-9.00% mol/Ls), (7.00-9.00%'s diamino-pyridine rubs You/liter), citric acid（0.40-0.60 mol/Ls）It is dissolved in toluene solution, 17h-19h is reacted, obtains compound 9.Nuclear-magnetism is total The hydrogen that shakes is composed1H NMR (400 MHz, CDCl3) d 8.05 (m, 1H),7.68 (m, 1H),7.61(m, 1H),7.43 (m, 1H),7.21(m, 1H),6.99 (m, 1H),6.73 (m, 1H),3.73 (S, 1H);Carbon-13 nmr spectra13C NMR (100 MHz, CDCl3) δ 161.2, 154.0, 151.5, 149.8, 147.3,139.0, 130.3, 129.9, 129.0,127.0,122.6,126.7, 120.8, 119.7, 114.8, 111.2, 55.9。
Embodiment 4：
Compound 12（Fig. 1-e）Specific preparation method it is as follows, synthesis equation be Fig. 6：
（1）At room temperature, by compound 10（1.00-1.50 mol/L）、S8（0.50-1.00 mol/Ls）It is dissolved in N, N- bis- In methylformamide and triethylamine solution, reacts 3-4 days, obtain compound 11；
（2）In 110 DEG C -115 DEG C, oxygen atmosphere, by chemical combination 11（1.00-1.05 mol/L）, cyclohexanone analog compound （5.50-6.00 mol/L）, palladium trifluoroacetate (7.00-9.00% mol/Ls), (7.00-9.00%'s diamino-pyridine rubs You/liter), citric acid（0.40-0.60 mol/Ls）It is dissolved in toluene solution, 17h-19h is reacted, obtains compound 12.Nuclear-magnetism is total The hydrogen that shakes is composed1H NMR (400 MHz, CDCl3) d 8.65 (d, 1H), 8.05 (d, 1H),7.68(d, 1H),7.61(d, 1H),7.43 (d, 1H),7.60 (d, 1H),7.2(s, 1H),7.0 (d, 1H);Carbon-13 nmr spectra13C NMR (100 MHz, CDCl3) δ 154.5, 149.9, 147.4, 147.1, 139.7, 129.9, 129.0, 128.23, 128.2, 127.0, 123.2, 121.6。
Embodiment 5：
Compound 15（Fig. 1-f）Specific preparation method it is as follows, synthesis equation be Fig. 7：
（1）At room temperature, by compound 13（1.00-1.50 mol/L）、S8（0.50-1.00 mol/Ls）It is dissolved in N, N- bis- In methylformamide and triethylamine solution, reacts 3-4 days, obtain compound 14；
（2）In 110 DEG C -115 DEG C, oxygen atmosphere, by compound 14（1.00-1.05 mol/L）, cyclohexanone analog compound （5.50-6.00 mol/L）, palladium trifluoroacetate (7.00-9.00% mol/Ls), (7.00-9.00%'s diamino-pyridine rubs You/liter), citric acid（0.40-0.60 mol/Ls）It is dissolved in toluene solution, 17h-19h is reacted, obtains compound 15.Nuclear-magnetism is total The hydrogen that shakes is composed1H NMR (400 MHz, CDCl3) d 8.65 (d, 1H), 8.05 (d, 1H),7.68 (d, 1H),7.61 (d, 1H),7.60 (d, 1H),7.43 (d, 1H),7.4(s, 1H),6.3 (d, 1H);Carbon-13 nmr spectra13C NMR (100 MHz, CDCl3) δ 154.5, 147.4, 149.9, 147.1, 144.1, 138.5, 129.9, 129.3 , 129.0, 125.2, 123.2, 121.4, 108.8。
Embodiment 6：
Compound 18（Fig. 1-g）Specific preparation method it is as follows, synthesis equation be Fig. 8：
（1）At room temperature, by compound 16（1.00-1.50 mol/L）、S8（0.50-1.00 mol/Ls）It is dissolved in N, N- bis- In methylformamide and triethylamine solution, reacts 3-4 days, obtain compound 17；
（2）In 110 DEG C -115 DEG C, oxygen atmosphere, by compound 17（1.00-1.05 mol/L）, cyclohexanone analog compound （5.50-6.00 mol/L）, palladium trifluoroacetate (7.00-9.00% mol/Ls), (7.00-9.00%'s diamino-pyridine rubs You/liter), citric acid（0.40-0.60 mol/Ls）It is dissolved in toluene solution, 17h-19h is reacted, obtains compound 18.Nuclear-magnetism is total The hydrogen that shakes is composed1H NMR (400 MHz, CDCl3) d 8.65 (d, 1H),8.05 (d, 1H),7.68 (d, 1H),7.61 (d, 1H),7.60 (d, 1H),7.43 (d, 1H),7.30(d, 1H),7.25(d, 1H),7.19(s, 1H),6.93(d, 1H);Carbon-13 nmr spectra13C NMR (100 MHz, CDCl3) δ 163.4, 154.0, 151.5,147.3, 149.8, 139.6, 130.9, 129.9,128.3,127.0, 126.7, 123.0, 122.6,120.8, 116.0, 115.8。

Claims (11)

1. one kind is such as（Fig. 1-a）Shown in nitrogenous, sulphur fused ring compound semi-conducting material；
Wherein, Ar is alkyl, alkoxy, aryl；
According to currently preferred,
The alkyl be selected from methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, Dodecyl, tridecyl, myristyl, pentadecyl, cetyl, heptadecyl or octadecyl；
The alkoxy be selected from methoxyl group, ethyoxyl, propoxyl group, butoxy, amoxy, hexyloxy, oxygroup in heptan, octyloxy, Nonyl epoxide, decyloxy, hendecane epoxide, dodecyloxy, tridecane epoxide, tetradecyloxyaniline, pentadecane epoxide, hexadecane oxygen Base, heptadecane epoxide or octadecane epoxide；
The aryl is selected from phenyl, naphthalene, thiophene, furans, halogeno-benzene, tolyl, ethylphenyl, propyl phenyl, butyl benzene Base, amyl phenyl, hexyl phenyl, heptyl phenyl, octyl phenyl, nonyl phenyl, decyl phenyl, undecyl phenyl, dodecane Base phenyl, tridecyl phenyl, myristyl phenyl, pentadecylphenyl, cetyl phenyl, heptadecyl phenyl or 18 Alkyl phenyl.
2. device according to claim 1, the wherein compound are oligomer.
3. device according to claim 1, wherein compound are polymer.
4. thin film transistor (TFT), it includes the devices according to any one of the above claim.
5. optical device, it includes right thin film transistor (TFT)s according to claim 4.
6. electroluminescent device, it includes thin film transistor (TFT)s according to claim 5.
7. being used to form the solution of thin film transistor (TFT), which includes solute, which includes as described in claim 1 organic Semiconducting compound.
8. solution according to claim 7, it includes solvent, solvent is selected from the benzene of substitution.
9. solution according to claim 8, the wherein solvent are replaced by one or more substituent groups selected from halogen and alkyl Benzene.
10. the method for being used to form transistor, this method include will be to apply according to the solution of claim 7 or claim 8 In on substrate.
11. method according to claim 10, the wherein solution are applied by ink jet printing.
CN201810372779.8A 2018-04-24 2018-04-24 A kind of preparation method and application of nitrogenous, sulphur fused ring compound Withdrawn CN108623613A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004058772A1 (en) * 2002-12-26 2004-07-15 Daiichi Suntory Pharma Co.,Ltd. Dihydrothienoquinoline derivatives and cell adhesion inhibitors containing the same
CN101348491A (en) * 2008-09-11 2009-01-21 中国科学院化学研究所 Phenyl ethylene end capped tetrathiophen derivative, preparation and use thereof
CN102206225A (en) * 2011-04-08 2011-10-05 中国科学院长春应用化学研究所 Polymer semiconducting material and organic thin film transistor
CN104125951A (en) * 2012-02-22 2014-10-29 捷恩智株式会社 Novel chalcogen-containing organic compound and use thereof
CN105330613A (en) * 2015-11-20 2016-02-17 哈尔滨工业大学（威海） Oxathiadiazole-2-oxide compound and preparation method thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004058772A1 (en) * 2002-12-26 2004-07-15 Daiichi Suntory Pharma Co.,Ltd. Dihydrothienoquinoline derivatives and cell adhesion inhibitors containing the same
CN101348491A (en) * 2008-09-11 2009-01-21 中国科学院化学研究所 Phenyl ethylene end capped tetrathiophen derivative, preparation and use thereof
CN102206225A (en) * 2011-04-08 2011-10-05 中国科学院长春应用化学研究所 Polymer semiconducting material and organic thin film transistor
CN104125951A (en) * 2012-02-22 2014-10-29 捷恩智株式会社 Novel chalcogen-containing organic compound and use thereof
CN105330613A (en) * 2015-11-20 2016-02-17 哈尔滨工业大学（威海） Oxathiadiazole-2-oxide compound and preparation method thereof

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