CN107501295B - Semiconductor material with triphendioxazine imide structure and preparation method thereof - Google Patents

Semiconductor material with triphendioxazine imide structure and preparation method thereof Download PDF

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CN107501295B
CN107501295B CN201710760451.9A CN201710760451A CN107501295B CN 107501295 B CN107501295 B CN 107501295B CN 201710760451 A CN201710760451 A CN 201710760451A CN 107501295 B CN107501295 B CN 107501295B
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imide
triphendioxazine
aromatic hydrocarbon
semiconductor material
dibromo
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CN107501295A (en
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肖义
王赫麟
陈令成
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Dalian University of Technology
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    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Abstract

A semiconductor material with a triphendioxazine imide structure and a preparation method thereof belong to the technical field of organic synthesis. The material is a novel triphendioxazine imide derivative with large conjugation and space distortion. The compound is synthesized by introducing aromatic structures with larger conjugated planes at 6-position and 14-position of monobromo or dibromo triphendioxazine imide and respectively reacting the aromatic structures with aromatic hydrocarbon monoboronate or aromatic hydrocarbon monoppinacol borate or aromatic hydrocarbon monotributyl tin through a C-C coupling method. The novel triphendioxazine imide semiconductor material has excellent solubility in common organic solvents, strong absorption in a visible light region, higher molar extinction coefficient, good redox property and electron transmission performance, and can be applied to the field of organic photoelectricity.

Description

Semiconductor material with triphendioxazine imide structure and preparation method thereof
Technical Field
The invention relates to the field of organic synthesis, in particular to a semiconductor material with a triphendioxazine imide structure and a preparation method thereof.
Background
Triphendioxazine imide is a kind of multi-element heterocyclic compound formed by using 5-amino-6-hydroxyphthalimide and 2, 5-hydroxyphthalimide through the processes of dehydration condensation and high-temp. ring closure. The triphendioxazine imide structure has a large conjugated plane, so that molecules are promoted to have a strong pi-pi conjugated effect, and the existence of the imide structures on the two sides improves the electron affinity of the molecules, so that the molecules have the characteristic of high electron mobility. The triphendioxazine imide has strong absorption in a visible light region and a high molar extinction coefficient, has good light stability and thermal stability, and can be applied to the field of organic semiconductors as an electronic transmission material, such as organic thin-film solar cells, organic field effect transistors, organic electroluminescent diodes, organic lasers and the like. Therefore, the development of the triphendioxazine imide derivative with a new structure has certain theoretical and practical significance.
Disclosure of Invention
The invention aims to introduce aromatic structures with large conjugated planes into 6-position and 14-position of triphendioxazine imide to obtain a novel triphendioxazine imide derivative with large conjugation and space distortion.
The invention provides a semiconductor material with a triphendioxazine imide structure, which has a general formula (I)
Figure BDA0001393025190000011
In the formula (I), R ═ C1～C20Straight chain alkane, C1～C20Branched alkanes,
Figure BDA0001393025190000021
Figure BDA0001393025190000022
Wherein n is 1, 2 or 3; r2Is H, C1～C20Straight chain alkane or C1～C20A branched alkane; r3Is CH3、CH(CH3)2、CH2CH(CH3)2、CH(CH3)CH2CH3Phenyl or benzyl; r4Is H, C1～C20Straight chain alkane or C1～C20A branched alkane; ar (Ar)2Is H or Ar1。
The material in the general formula (I) can be prepared by the following process:
(1)
wherein X ═ H or Br; r ═ C1～C20Straight chain alkane, C1～C20Branched alkanes,
Figure BDA0001393025190000024
Wherein n is 1, 2 or 3; r2Is H, C1～C20Straight chain alkane or C1～C20A branched alkane; r3Is CH3、CH(CH3)2、CH2CH(CH3)2、CH(CH3)CH2CH3Phenyl or benzyl; r4Is H, C1～C20Straight chain alkane or C1～C20A branched alkane; ar (Ar)2When X is H, Ar2Is H; when X is Br, Ar2Is Ar1。
The preparation method of the semiconductor material containing the triphendioxazine imide structure comprises the following steps:
the method is characterized in that monobromo or dibromo triphendioxazine imide and substituted aromatic hydrocarbon are used as raw materials, the molar ratio of the monobromo or dibromo triphendioxazine imide to the substituted aromatic hydrocarbon is 1: 1-10, and Pd (PPh)3)4、Pd(PPh3)2Cl2、Pd(dppf)Cl2、Pd(CH3COO)2Or Pd2(dba)3The molar ratio of the mono-bromine or double-bromine triphendioxazine imide to the catalyst is 1: 0.01-0.4, and the molar ratio of the mono-bromine or double-bromine triphendioxazine imide to the catalyst is 0.1-2M of Na2CO3、K2CO3、NaOH、CH3COONa、CH3COOK、KHCO3、K2HPO4Or K3PO4And (3) as an alkali source, stirring and reacting in an organic solvent for 2-30 hours at 60-150 ℃, and performing C-C coupling reaction to obtain the triphendioxazine imide derivative with the general formula (I). Wherein the organic solvent is selected from one or more of methanol, ethanol, toluene, chlorobenzene, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone.
The material obtained by the above-mentioned method can be isolated by a conventional method such as solution recrystallization, precipitation and filtration, silica gel column chromatography, spray drying and the like.
The invention has the beneficial effects that: the compound of the invention has excellent solubility in common organic solvents, is easy to dissolve in organic solvents such as dichloromethane, tetrahydrofuran, chloroform, toluene, chlorobenzene and the like, and can be used for preparing a medicament for treating the tumorThe solubility of dichloromethane and chloroform is more than 30mg/mL, so that the problem that large-structure molecules are not easy to dissolve in an organic solvent is avoided; the material has stronger absorption peak and higher molar extinction coefficient in a 300-600nm visible light region, and the molar extinction coefficient can reach 5 multiplied by 104M-1cm-1The good visible light capturing performance meets the requirements of the organic photoelectric material on absorption intensity and light absorption area; the material also has good redox characteristics, and the lowest unoccupied orbital (LUMO) of the material is tested and calculated to be about-3.9-4.0 eV by cyclic voltammetry, so that the material is proved to have strong electron accepting capability; the electron mobility of the material is tested by using a Space Charge Limited Current (SCLC) method, the prepared organic thin film device can show excellent electron transmission performance, and the electron mobility of the material can reach 1 x 10-3cm2V-1s-1. The invention can be applied to the field of organic photoelectricity, such as: organic photodetectors, organic thin film solar cells, organic field effect transistors, organic electroluminescent diodes, organic lasers, complementary circuits, and uses related thereto.
The invention is illustrated but not limited by the following examples in which all parts and percentages are by weight unless otherwise indicated.
Drawings
FIG. 1 is an absorption spectrum in nanometers of a methylene chloride solution of the product of example 1, with wavelength on the abscissa; the ordinate is the molar extinction coefficient. The product has a maximum absorption wavelength of 542nm and a molar absorption coefficient of 5.37 × 104M-1cm-1。
FIG. 2 is a cyclic voltammogram of a solution of the product of example 1 in methylene chloride with voltage on the abscissa and in volts; the ordinate is the current in microamps. The material has three groups of reversible oxidation reduction peaks, no oxidation peak, the half-wave potential of the first reduction peak is-1.14V, and the energy level of the low unoccupied orbital of the material is calculated to be-3.94 eV.
FIG. 3 is a graph of the current density versus voltage for the product of example 1 tested for electron mobility using space charge limited currentCurve line. The abscissa is voltage in volts; the ordinate is the current density in amperes per square centimeter. The real square points are actually measured curves, the empty points of the triangles are theoretical formula fitting curves, the two curves have good coincidence, and the actually measured curves are proved to be real and credible. The electron mobility was calculated to be 4.05X 10 by Mott-Gurney's equation-3cm2V-1s-1。
Detailed Description
The following detailed description of the embodiments of the invention refers to the accompanying drawings.
Example 1
Figure BDA0001393025190000051
Bis-bromotriphendioxazine imide (1.00mmol), phenanthrene monoborate (6.00mmol), Pd (dppf) Cl2(0.1mmol) and 1M Na2CO3Adding the aqueous solution (12.00mmol) into a reactor, taking tetrahydrofuran as a solvent, heating to react for 6h at 80 ℃, determining the reaction end point through thin plate chromatography, and stopping the reaction. Dichloromethane and water liquid are washed, dried, desolventized and purified by silica gel column chromatography to obtain pink solid, and the yield is as follows: 76%, HRMS: 1336.7914 (m/z).
Example 2
Figure BDA0001393025190000052
Monobromotribenzene dioxazine imide (1.00mmol), naphthalene monoborate (4.00mmol), Pd (PPh)3)4(0.2mmol) and 1M K2CO3Adding the aqueous solution (20.00mmol) into a reactor, heating and reacting for 2h at 70 ℃ by using methanol as a solvent, determining the reaction end point by thin plate chromatography, and stopping the reaction. Dichloromethane and water liquid are washed, dried, desolventized and purified by silica gel column chromatography to obtain pink solid, and the yield is as follows: 74%, HRMS: 1028.5428 (m/z).
Example 3
Figure BDA0001393025190000061
Bis-bromotriphendioxazine imide (1.00mmol), monottributyltin thiophene (10.00mmol) and Pd (PPh)3)4(0.4mmol) is added into a reactor, toluene is taken as a solvent, the mixture is heated and reacted for 4 hours at the temperature of 110 ℃, the reaction end point is determined by thin plate chromatography, and the reaction is stopped. Washing dichloromethane and water solution, drying, removing solvent, purifying by silica gel column chromatography to obtain mauve solid, wherein the yield is as follows: 80%, HRMS: 1236.6277 (m/z).
Example 4
Figure BDA0001393025190000062
Monobromotribenzene dioxazine imide (1.00mmol), triphenylamine monoborate (1.00mmol), Pd (PPh)3)2Cl2(0.01mmol) and 2M K2HPO4Adding the aqueous solution (3.00mmol) into a reactor, heating N, N-dimethylformamide as a solvent at 60 ℃ for 10h, carrying out thin-plate chromatography to determine the reaction end point, and stopping the reaction. Washing dichloromethane and water solution, drying, removing solvent, purifying by silica gel column chromatography to obtain mauve solid, wherein the yield is as follows: 71%, HRMS: 1063.4735 (m/z).
Example 5
Figure BDA0001393025190000063
Bis-bromo-triphenyl-dioxazine imide (1.00mmol), monoboronic acid ester carbazole (6.00mmol), Pd (PPh)3)2Cl2(0.02mmol) and 0.5M CH3Adding COOK aqueous solution (12.00mmol) into a reactor, heating N, N-dimethylacetamide as a solvent at 120 ℃ for 8h, carrying out thin plate chromatography to determine the reaction end point, and stopping the reaction. Washing dichloromethane and water solution, drying, removing solvent, purifying by silica gel column chromatography to obtain mauve solid, wherein the yield is as follows: 76%, HRMS: 1412.7019 (m/z).
Example 6
Figure BDA0001393025190000071
Monobromotribenzene dioxazine imide (1.00mmol), monoboronic acid ester fluorenone (5.00mmol), Pd (CH)3COO)2(0.08mmol) and 0.5M K3PO4Adding the aqueous solution (10.00mmol) into a reactor, heating and reacting for 6h at 80 ℃ by using ethanol as a solvent, determining the reaction end point by thin plate chromatography, and stopping the reaction. Washing dichloromethane and water solution, drying, removing solvent, purifying by silica gel column chromatography to obtain mauve solid, wherein the yield is as follows: 73%, HRMS: 1192.6626 (m/z).
Example 7
Figure BDA0001393025190000072
Bis (bromotriphendioxazine) imide (1.00mmol), fluorene monoborate (8.00mmol) and Pd (CH)3COO)2(0.2mmol) and 0.1M NaOH aqueous solution (16.00mmol) are added into a reactor, glycol dimethyl ether is taken as a solvent, the reaction is heated for 8 hours at 100 ℃, the end point of the reaction is determined by thin plate chromatography, and the reaction is stopped. Dichloromethane and water liquid are washed, dried, desolventized and purified by silica gel column chromatography to obtain pink solid, and the yield is as follows: 70%, HRMS: 1538.9688 (m/z).
Example 8
Figure BDA0001393025190000081
Monobromotribenzene dioxazine imide (1.00mmol), monotributyltin dithiophene pyrrolopyrrole dione (3.00mmol) and Pd2(dba)3(0.2mmol) is added into a reactor, chlorobenzene is used as a solvent, the mixture is heated and reacted for 4 hours at the temperature of 150 ℃, the reaction end point is determined by thin plate chromatography, and the reaction is stopped. Washing dichloromethane and water solution, drying, removing solvent, purifying by silica gel column chromatography to obtain mauve solid, wherein the yield is as follows: 72%, HRMS: 1230.4807 (m/z).
Example 9
Figure BDA0001393025190000082
Bis-bromotriphendioxazine imide (1.00mmol), monoboronic perylene monoimide (5.00mmol) and Pd2(dba)3(0.1mmol) and 1.5M CH3Adding COONa aqueous solution (10.00mmol) into a reactor, heating N-methylpyrrolidone as a solvent at 80 ℃ for 24 hours, carrying out thin plate chromatography to determine the reaction end point, and stopping the reaction. Dichloromethane and water liquid are washed, dried, desolventized and purified by silica gel column chromatography to obtain pink solid, and the yield is as follows: 75%, HRMS: 2043.2655 (m/z).
Example 10
Figure BDA0001393025190000083
Monobromotribenzene dioxazine imide (1.00mmol), monoboronic ester perylene imide (5.00mmol), Pd2(dba)3(0.2mmol) and 1.2M KHCO3Adding the aqueous solution (10.00mmol) into a reactor, heating ethylene glycol monomethyl ether as a solvent at 80 ℃ for reaction for 30h, determining the reaction end point by thin plate chromatography, and stopping the reaction. Dichloromethane and water liquid are washed, dried, desolventized and purified by silica gel column chromatography to obtain pink solid, and the yield is as follows: 78%, HRMS: 1823.1323 (m/z).
Example 11
Ultraviolet and visible absorption spectrum test, and the used instrument model is a U.S. HP8453 type ultraviolet spectrophotometer. The product of example 1 was weighed out accurately and diluted to 1X 10-5M in dichloromethane, at room temperature using a 1cm glass cuvette cell. Wherein the molar extinction coefficient (ε) of the material is determined using the formula: a ═ epsilon cb, calculated, and a is the absorbance of the maximum absorption peak; c is the mass concentration of the material; b is the thickness of the cuvette cell used. Optical bandgap by absorption maximum sideband method according to equation Eg＝1024/λmaxeV was calculated. The maximum absorption wavelength of the product is 542nm, the absorption range is 300-600nm, and the molar absorption coefficient is calculated to be 5.37 multiplied by 104M-1cm-1Optical band gap Eg2.19eV, and the material is proved to have excellent visible light capturing performance.
Example 12
Cyclic voltammetry using an instrument model BSA100B/W electrochemical analysis system. A three-electrode test system is adopted, and a glassy carbon electrode is used as a working electrode; a saturated calomel electrode is used as a reference electrode; a platinum wire electrode is used as a counter electrode; the product of example 1 was accurately weighed and prepared as a10 mg/mL solution in methylene chloride, and tetrabutylammonium hexafluorophosphate was added as an electrolyte. Using ferrocene as an internal standard couple, reference is made to the document ferrocene couple at an absolute value of 5.08eV relative to vacuum, according to equation ELUMO＝-(5.08+Eonset re) eV, the cyclic voltammetry curve of the material obtains the half-wave potential (E) of the first reduction peak thereofonset re) The LUMO energy level was calculated to be-3.94 eV for-1.14V, and then calculated according to equation EHOMO＝(ELUMO-Eg) eV estimates that the highest occupied orbital (HOMO) energy level is-6.13 eV, and the material is proved to have good oxidation-reduction characteristics.
Example 13
The space charge current-limiting method is used for testing the electron mobility of the organic semiconductor material, and the model of the instrument is a Keithley model 2400 (I-V) digital source table in the United states. The device structure of the single-electron device is as follows: ITO/ZnO/Active layer/Ca/Al, the manufacturing method of the device comprises the following steps: the ITO substrate is sequentially ultrasonically cleaned by ethanol, acetone and ultrapure water; after nitrogen purging is carried out, carrying out ozone treatment for 30 minutes; spin coating 0.25M zinc oxide to a thickness of about 20 nm; annealing at 200 deg.C in air for 1 hr, and spin-coating compound chloroform solution in glove box at concentration of 20mg/mL and thickness of about 200 nm; transferring the spin-coated substrate into a vacuum evaporation chamber with vacuum degree of 1 × 10-4Depositing Ca (10nm)/Al (100nm) electrode at Pa; the resulting devices were tested for current density-voltage curves using a digital source meter. Electron mobility according to Mott-Gurney formula:
Figure BDA0001393025190000101
wherein J represents current density; epsilonrThe dielectric constant of the representative material (this value can be set to 3 in an organic semiconductor); epsilon0Represents the vacuum permittivity; mu represents the electricity of the materialA mobility; l represents the thickness of the active layer; v represents the voltage applied across the active terminals. According to J1/2And the electron mobility of the material can be calculated according to a curve of vs V. And fitting a corresponding curve by using SigmaPlut software according to a Mott-Gurney formula, wherein the fitted curve is identical with the measured value, and the fact that the test data is real and credible is shown. The electron mobility of the material is calculated to be 4.05 multiplied by 10 through Mott-Gurney formula-3cm2V-1s-1The material is proved to have excellent electron transmission performance.

Claims (2)

1. The semiconductor material with the structure of triphendioxazine imide is characterized in that the general formula of the material is as follows:
Figure DEST_PATH_IMAGE001
（Ⅰ）
in the formula (I), R = C20A branched alkane; ar (Ar)1=
Figure 424389DEST_PATH_IMAGE002
；R4Is H; ar (Ar)2Is Ar1。
2. The method for preparing the semiconductor material with the triphendioxazine imide structure according to claim 1, wherein the method comprises the following steps: synthesizing the dibromine triphendioxazine imide and substituted aromatic hydrocarbon by a C-C coupling method to obtain a target molecule; the substituted aromatic hydrocarbon is monoboronic aromatic hydrocarbon, monoppinacol boric acid ester aromatic hydrocarbon or monotributyl tin aromatic hydrocarbon, and the specific reaction general formula is as follows:
(1) carrying out a suzuki coupling reaction on the dibromo triphendioxazine imide and aromatic hydrocarbon monoboronate:
Figure DEST_PATH_IMAGE003
(2) carrying out suzuki coupling reaction on the dibromo triphendioxazine imide and the monoppinacol boric acid ester aromatic hydrocarbon:
Figure 341529DEST_PATH_IMAGE004
(3) carrying out stille coupling reaction on the dibromo triphendioxazine imide and mono tributyltin aromatic hydrocarbon:
Figure DEST_PATH_IMAGE005
wherein X = Br; r = C20A branched alkane; ar (Ar)1=；R4Is H; ar (Ar)2Is Ar1。
The method comprises the following specific steps: adding dibromo triphendioxazine imide, substituted aromatic hydrocarbon, catalyst and alkali into a reactor, wherein the reaction temperature is 60-150 DEG CoUnder the condition of C, stirring and reacting in an organic solvent for 2-30 hours to obtain the triphendioxazine imide derivative with the general formula (I);
the molar ratio of the dibrominated triphendioxazine imide to the substituted aromatic hydrocarbon is 1: 1-10, the molar ratio of the dibrominated triphendioxazine imide to the catalyst is 1:0.01 ~ 0.4.4, and the molar ratio of the monoboronic aromatic hydrocarbon or the monoppinacol borate aromatic hydrocarbon to the alkali is 1: 2 ~ 5;
the catalyst is Pd (PPh)3)4、Pd(PPh3)2Cl2、Pd(dppf)Cl2、Pd(CH3COO)2Or Pd2(dba)3(ii) a The alkali is Na2CO3、K2CO3、NaOH、CH3COONa、CH3COOK、KHCO3、K2HPO4Or K3PO4(ii) a The organic solvent is one or more of methanol, ethanol, toluene, chlorobenzene, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, N-dimethylformamide, N-dimethylacetamide or N-methylpyrrolidone.
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