CN110105369A - A kind of preparation method and application of two pyrazines fused ring compound - Google Patents

A kind of preparation method and application of two pyrazines fused ring compound Download PDF

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CN110105369A
CN110105369A CN201910418837.0A CN201910418837A CN110105369A CN 110105369 A CN110105369 A CN 110105369A CN 201910418837 A CN201910418837 A CN 201910418837A CN 110105369 A CN110105369 A CN 110105369A
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刘颖
隋颜泽
高腾
吴彦超
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Harbin Institute of Technology Weihai
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    • 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
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    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • 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
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    • C09K2211/1018—Heterocyclic compounds
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Abstract

The present invention provides the synthetic methods and application of a kind of two pyrazine fused ring compounds and its derivative, i.e. general formula is the compound of Fig. 1, which includes the semiconducting compound such as flowering structure, wherein R1And R2It can be the same or different, and it is selected from substituent R, which is the straight chain optionally replaced (i) with 1 to 20 carbon atom, branching or cyclic alkyl chain, alkoxy, amino, acylamino-, silicyl or alkenyl, or (ii) polymerizable or reactive group, the group are selected from ester, alkylidene and the stannyl of halogen, boric acid, hypoboric acid and boric acid and hypoboric acid.Z independently is S, O, Se, NR`, and wherein R` is H or substituent group.The organic semiconductor compound is used as active layer in organic semiconductor device such as thin film transistor (TFT).

Description

A kind of preparation method and application of two pyrazines fused ring compound
Technical field
The present invention relates to a kind of preparation method and applications of two pyrazine fused ring compounds.
Background technique
In recent years, molecule base conjugated material arouses widespread concern, such as some containing sulphur, nitrogen, the thienyl of oxygen, The heterocycles such as pyridyl group, pyrrole radicals and furyl small organic molecule and its macromolecule, these materials are in organic semiconducting materials and electricity There is good application in terms of sub- device, novel pi-conjugated organic semi-conductor design and synthesis have attracted more and more researchs The concern of person, because they have potential application value in various photoelectric devices.It is especially linearly condensed and Ring class molecule can be applied to organic field effect tube (OFETs), light emitting diode (LEDs) and photovoltaic cell (Anthony, J. E. Chem. Rev. 2006,106,5028.).
Research interest in recent years focuses primarily upon pentacene and its derivative.Existing research shows (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 device made of/Si substrate deposition shows that outstanding charge carries Stream transport factor is 1.5 cm2/(V·s).But there is many defects when pentacene is applied to device, such as poor solubility, Limited stability and the accumulation unfavorable in solid-state in air, overcoming a strategy of these defects is in condensed ring system Introducing hetero-atoms construct more stable trapezoidal condensed molecule.Sulphur shows various points as the introducing of thiophene-structure Interaction between son, such as Van der Waals force, pi-pi accumulation and sulphur-sulphur interaction, these all play one to high mobility is obtained Fixed effect.In addition, the introducing of nitrogen-atoms can be good at the stability of reinforcing material.
Using organic semiconductor compared to used to date in organic field thin film transistor (OTFT) Inorganic semiconductor have the advantages that it is some they can be processed in the form of any from fiber to film, there is high mechanical flexibility, energy It is produced with low cost and light-weight.For example, being at first polythiophene in addition, poly- (3- hexyl) thiophene to the report of polyheterocycle base OTFT And a, a- dialkyl group Uniformpoly thiophene are the high mobility polymer occurred at first and small molecule respectively.To these chemical combination between the several years The chemical modification (variation including ring ring connectivity and substitution form) of object has obtained quite a lot of electroactive material.
But there is many defects when being applied to device, for example, poor solubility, in air limited stability and It is that introducing hetero-atoms are more stable to construct in condensed ring system that the unfavorable accumulation of solid-state, which overcomes a strategy of these defects, Trapezoidal condensed molecule.Sulphur shows various intermolecular interactions, such as Van der Waals as the introducing of thiophene-structure Power, π pi accumulation and the interaction of sulphur sulphur, these all play a role to high mobility is obtained.In addition, nitrogen-atoms Introduce the stability that can be good at reinforcing material.
Since conducting polymer is found, organic semiconductor is because of scene effect transistor, light emitting diode and light Volt field of batteries has huge application prospect and attracts attention.Compared to inorganic material, not only structure can be cut organic material, property The advantages that energy is adjustable, while being also equipped with low cost, reduction process temperature, solution processable, flexible.But unlike that inorganic semiconductor Continuous band structure, organic semi-conductor energy level be it is discrete, charge transmission dependent on carrier from a molecular transport to The ability of another molecule, and this and packing of molecules, energy level and band gap are closely bound up, (Wang chengliang etc. Chem.Soc.Rev., 2018,47,422--500).
Summary of the invention
It is an object of that present invention to provide the preparation method and applications of a kind of nitrogenous, oxygen, the fused ring compound of sulphur.For existing The deficiency of technology, the present invention is intended to provide a kind of preparation method of two pyrazine fused ring compounds of nitrogenous, oxygen, sulphur, by its preparation Condensed conjugated material have excellent solubility property and carrier transmission performance, be dissolved in organic solvent, then apply On the substrates such as ito glass, silicon wafer or ceramics, it is capable of forming after heating anneal appropriate processing soft, high-sequential Transparent membrane；Pi-conjugated structure big simultaneously is conducive to carrier transport, therefore the present invention also provides a kind of nitrogenous, sulphur condensed ring Application of the compound in Organic Thin Film Transistors field.It is realized by two pyrazine fused ring compound (Fig. 1) of general formula.
Wherein R1And R2, can be the same or different, and be selected from substituent R, which is (i) to have 1 to 20 The straight chain of carbon atom optionally replaced, branching or cyclic alkyl chain, alkoxy, amino, acylamino-, silicyl or alkenyl, Or (ii) polymerizable or reactive group, the group are selected from ester, the Asia of halogen, boric acid, hypoboric acid and boric acid and hypoboric acid Alkyl and stannyl.Z independently is S, O, Se, NR`, and wherein R` is H or substituent group.
Detailed description of the invention
Fig. 1 is a kind of structure chart of two pyrazine fused ring compounds；
Fig. 2 is reaction synthetic route general formula figure；
Fig. 3 is the synthetic route chart of compound 1；
Fig. 4 is the synthetic route chart of compound 2；
Fig. 5 is the synthetic route chart of compound 3；
Fig. 6 is the synthetic route chart of compound 4.
Specific embodiment
Its reaction process is as shown in Figure 2.
Starting material is commercially available, known compound or easily prepared intermediate be by using this field skill in the literature Standard synthetic methods known to art personnel and program preparation.The standard for preparing organic molecule and functional group conversion and transformation is closed It can easily be obtained by this field related science document or standard textbook at methods and procedures.It should be understood that when to the source of an allusion When type or preferred process conditions (i.e. reaction temperature, time, reactant molar ratio, solvent, pressure etc.), unless otherwise stated, Also other process conditions can be used.Optimum reaction condition can change with specific reactants used or solvent, but such Part can be determined by those skilled in the art by routine optimisation procedures.Organic synthesis field technical staff will be recognized in order to excellent Change the formation of compound described herein, thus it is possible to vary the property and sequence of provided synthesis step, the method for the invention can With any appropriate method monitoring known according to this field.Such as spectrum means such as nuclear magnetic resonance spectrometry (MR, example can be passed through Such as H or C), infra-red sepectrometry (IR), spectrophotometry (such as UV- is visible), mass spectrography (MS) or pass through chromatography such as high pressure liquid Chromatography (HPLC), gas chromatography (GC), the shape of gel permeation chromatography (GPC) or thin-layered chromatography (TLC) monitoring product At reaction described herein or method can carry out in the suitable solvent that can be readily selected by organic synthesis field technical staff. Suitable solvent usually at a temperature of reacting carried out, i.e., can be solvent freezing point to solvent boiling point at a temperature of to anti- Answering object, intermediate and/or product substantially does not have reactivity.Given reaction can be in a kind of solvent or in the mixed of more than one solvent It closes and is carried out in object.Depending on specific reaction step, the solvent for being suitble to specific reaction step can choose, two Pyrazines are preferable It is prepared using shown in following reaction scheme Fig. 2:
Step (a) (b) (c) (d) (e) is described in
(a) (b) and (d) is described in Zou Yingping, Adv. Funct. Mater. 2008,18,2724-2732；
(c) Yamamoto etc., Tetrahedron, 2018,74,5309-5318 are described in；
(e) it is described in the Tetrahedron such as Ahra Go 71 (2015) 1215-1226.
Embodiment 1:
The specific preparation method of compound is as follows, and synthesis equation is Fig. 3:
(1) at 50 DEG C, by thiophene (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 mol/L), nitric acid (4.00- 5.00 mol/Ls) it is mixed in chloroform, reaction obtains compound 2,5- dinitro thiophene in 1-2 days；
(2) 80-110 DEG C by compound 2,5- dinitro thiophene (0.60-0.65 mol/L) and zinc granule (120-200 grams/ Rise) it is added in hydrochloric acid, compound intermediate product 2, bis- amido thiophene of 5- are obtained after carrying out reduction；
(3) at 15-30 DEG C, under the atmosphere of argon gas protection, by compound 2, bis- amido thiophene of 5- (0.75-0.85 moles/ Rise) it is dissolved in ethanol solution, di-tert-butyl dicarbonate (1.50-1.70 mol/L) is added dropwise and reacts 10-30 minutes, obtains chemical combination Object 2,5- di tert butyl carbonate amido thiophene；
(4) at 50 DEG C, by 2,5- di tert butyl carbonate amido thiophene (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 moles/ Rise), nitric acid (4.00-5.00 mol/L) be mixed in chloroform, reaction obtains compound 2, bis- amido -3,4- bis- of 5- in 1-2 days Nitrothiophene；
(5) under nitrogen atmosphere, by compound 2, bis- amido -3,4- dinitro thiophene of 5- (1.00-1.20 mol/L), phenyl Diketone (2.00-4.40 mol/L), indium (1.00-1.20 mol/L), indium trichloride (1.00-1.20 mol/L) are dissolved in In methanol solution, it is stirred at reflux 10-20h.Obtain solid chemical combination phenyl substituted thiophene and two pyrazine compounds 1.
Embodiment 2:
The specific preparation method of compound is as follows, and synthesis equation is Fig. 4:
(1) at 50 DEG C, by thiophene (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 mol/L), nitric acid (4.00- 5.00 mol/Ls) it is mixed in chloroform, reaction obtains compound 2,5- dinitro thiophene in 1-2 days；
(2) 80-110 DEG C by compound 2,5- dinitro thiophene (0.60-0.65 mol/L) and zinc granule (120-200 grams/ Rise) it is added in hydrochloric acid, compound intermediate product 2, bis- amido thiophene of 5- are obtained after carrying out reduction；
(3) at 15-30 DEG C, under the atmosphere of argon gas protection, by compound 2, bis- amido thiophene of 5- (0.75-0.85 moles/ Rise) it is dissolved in ethanol solution, di-tert-butyl dicarbonate (1.50-1.70 mol/L) is added dropwise and reacts 10-30 minutes, obtains chemical combination Object 2,5- di tert butyl carbonate amido thiophene；
(4) at 50 DEG C, by 2,5- di tert butyl carbonate amido thiophene (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 moles/ Rise), nitric acid (4.00-5.00 mol/L) be mixed in chloroform, reaction obtains compound 2, bis- amido -3,4- bis- of 5- in 1-2 days Nitrothiophene；
(5) under nitrogen atmosphere, by compound 2, bis- amido -3,4- dinitro thiophene of 5- (1.00-1.20 mol/L), phenanthrenequione (2.00-4.40 mol/L), indium (1.00-1.20 mol/L), indium trichloride (1.00-1.20 mol/L) are dissolved in methanol In solution, it is stirred at reflux 10-20h.Obtain solid chemical combination phenanthryl fused thiophene and two pyrazine compounds 2.
Embodiment 3:
The specific preparation method of compound is as follows, and synthesis equation is Fig. 5:
(1) at 50 DEG C, by furans (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 mol/L), nitric acid (4.00- 5.00 mol/Ls) it is mixed in chloroform, reaction obtains compound 2,5- dinitro furans in 1-2 days；
(2) 80-110 DEG C by compound 2,5- dinitro furans (0.60-0.65 mol/L) and zinc granule (120-200 grams/ Rise) it is added in hydrochloric acid, compound intermediate product 2, bis- amido furans of 5- are obtained after carrying out reduction；
(3) at 15-30 DEG C, under the atmosphere of argon gas protection, by compound 2, bis- amido furans of 5- (0.75-0.85 moles/ Rise) it is dissolved in ethanol solution, di-tert-butyl dicarbonate (1.50-1.70 mol/L) is added dropwise and reacts 10-30 minutes, obtains chemical combination Object 2,5- di tert butyl carbonate amido furans；
(4) at 50 DEG C, by 2,5- di tert butyl carbonate amido furans (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 moles/ Rise), nitric acid (4.00-5.00 mol/L) be mixed in chloroform, reaction obtains compound 2, bis- amido -3,4- bis- of 5- in 1-2 days Nitrofuran；
(5) under nitrogen atmosphere, by compound 2, bis- amido -3,4- dinitro furans (1.00-1.20 mol/L) of 5-, hexamethylene Base diketone (2.00-4.40 mol/L), indium (1.00-1.20 mol/L), indium trichloride (1.00-1.20 mol/L) are molten In methanol solution, it is stirred at reflux 10-20h.Obtain solidification cyclization hexyl substituted furan and two pyrazine compounds 3.
Embodiment 4:
The specific preparation method of compound is as follows, and synthesis equation is Fig. 6:
(1) at 50 DEG C, by pyrroles's (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 mol/L), nitric acid (4.00- 5.00 mol/Ls) it is mixed in chloroform, reaction obtains compound 2,5- dinitro pyrroles in 1-2 days；
(2) 80-110 DEG C by compound 2,5- dinitro thiophene (0.60-0.65 mol/L) and zinc granule (120-200 grams/ Rise) it is added in hydrochloric acid, compound intermediate product 2, bis- amido pyrroles of 5- are obtained after carrying out reduction；
(3) at 15-30 DEG C, under the atmosphere of argon gas protection, by compound 2, bis- amido pyrroles of 5- (0.75-0.85 moles/ Rise) it is dissolved in ethanol solution, di-tert-butyl dicarbonate (1.50-1.70 mol/L) is added dropwise and reacts 10-30 minutes, obtains chemical combination Object 2,5- di tert butyl carbonate amido pyrroles；
(4) at 50 DEG C, by 2,5- di tert butyl carbonate amido pyrroles (1.00-1.20 mol/L), sulfuric acid (4.00-5.00 moles/ Rise), nitric acid (4.00-5.00 mol/L) be mixed in chloroform, reaction obtains compound 2, bis- amido -3,4- bis- of 5- in 1-2 days Nitro-pyrrole；
(5) under nitrogen atmosphere, by compound 2, bis- amido -3,4- dinitro pyrroles of 5- (1.00-1.20 mol/L), furans Base diketone (2.00-4.40 mol/L), indium (1.00-1.20 mol/L), indium trichloride (1.00-1.20 mol/L) are molten In methanol solution, it is stirred at reflux 10-20h.Obtain solid chemical combination furyl substituted thiophene and two pyrazine compounds 4.
Device preparation
Using top electrode structure, the Si/SiO of OTS modification2In substrate, high vacuum (2 × 10-4Pa Deposit organic semiconductor under) Layer.SiO with 500 nm thickness2Layer and 7.5 nF cm-2The n-type silicon wafer of capacitor is as grid.Source-drain electrode utilizes mask plate Gold electrode (50 nm) is deposited on organic semiconductor layer, ditch road widthW =8.8 mm, it is longL= 80 μm.Organic semiconductor film Deposition rate is gradually accelerated from 0.1/s to 0.4 ~ 0.6/s, and film thickness is detected by quartz crystal monitoring device, most Whole deposition thickness is 50 nm.The mobility [mu] of material can be obtained by the calculation formula of the mobility of saturation regionFET: the electricity of saturation region Stream-voltage relationship are as follows:I DS = (μ FET WC i /2L)(V G- V T)2, formula (1-1), the electrical property of device is in Keithley It is measured on 4200 SCS semiconductor analysis instrument.All measurements are at room temperature, carry out in atmosphere.

Claims (10)

1. Fig. 1 is two pyrazine fused ring compounds；Such compound is a kind of organic semiconductor device, the organic semiconductor device packet Semiconducting compound containing such as flowering structure, wherein R1And R2, can be the same or different, and be selected from substituent R, the substituent R It is the straight chain optionally replaced (i) with 1 to 20 carbon atom, branching or cyclic alkyl chain, alkoxy, amino, acylamino-, Silicyl or alkenyl, or (ii) polymerizable or reactive group, the group are selected from halogen, boric acid, hypoboric acid and boric acid With the ester, alkylidene and stannyl of hypoboric acid；Z is S, O, Se, NR`, and wherein R` is H or substituent group.
2. device according to claim 1, wherein the compound is oligomer.
3. thin film transistor (TFT), it includes the devices according to any one of the above claim.
4. optical device, it includes right thin film transistor (TFT)s according to claim 3.
5. electroluminescent device, it includes thin film transistor (TFT)s according to claim 4.
6. being used to form the solution of thin film transistor (TFT), which includes solute, which includes as described in claim 1 organic Semiconducting compound.
7. solution according to claim 6, it includes solvent, solvent is selected from the benzene replaced.
8. solution according to claim 7, wherein the solvent is replaced by one or more substituent groups selected from halogen and alkyl Benzene.
9. the method for being used to form transistor, this method includes that will be applied to according to the solution of claim 6 or claim 7 On substrate.
10. method according to claim 9, wherein the solution is applied by ink jet printing.
CN201910418837.0A 2019-05-20 2019-05-20 A kind of preparation method and application of two pyrazines fused ring compound Pending CN110105369A (en)

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