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CN110734451B - Semiconductor material, preparation method thereof and organic light-emitting diode - Google Patents

Semiconductor material, preparation method thereof and organic light-emitting diode Download PDF

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CN110734451B
CN110734451B CN201810789867.8A CN201810789867A CN110734451B CN 110734451 B CN110734451 B CN 110734451B CN 201810789867 A CN201810789867 A CN 201810789867A CN 110734451 B CN110734451 B CN 110734451B
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semiconductor material
electron
benzothiophene
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CN110734451A (en
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孟鸿
贺耀武
张天
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Peking University Shenzhen Graduate School
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Abstract

The invention discloses a semiconductor material, a preparation method thereof and an organic light-emitting diode, wherein the general molecular structural formula of the semiconductor material is

Description

Semiconductor material, preparation method thereof and organic light-emitting diode
Technical Field
The invention relates to the field of organic semiconductors, in particular to a semiconductor material, a preparation method thereof and an organic light-emitting diode.
Background
Organic Light Emitting Diodes (OLEDs) have a wide application prospect in the field of flexible display and illumination due to their advantages of low production cost, large-area fabrication, etc., and thus research on organic semiconductor materials applied to OLEDs has attracted attention from researchers.
The development of organic semiconductor materials featuring air stability, high hole mobility, and high luminous efficiency remains a challenge in this field. [1] Benzothiophene [3,2-b ] [1] benzothiophene (BTBT) as a classical semiconductor core has attracted considerable interest to researchers for its excellent device performance.
The furan derivative has potential application prospect in the field of luminescence due to unique properties, and furan is one of the simplest heterocyclic aromatic compounds and has very similar chemical structure and electronic properties with thiophene. However, thiophenes contain a relatively heavy sulfur atom, which leads to fluorescence quenching due to internal switching by spin-orbit coupling of the heavy atom. The furan semiconductor does not have the problem of fluorescence quenching caused by spin-orbit coupling effect, and has more excellent fluorescence property compared with thiophene semiconductor, so that the furan semiconductor can be used for preparing organic semiconductor light-emitting devices.
Thiophene derivatives have the characteristic of stronger carrier mobility, while furan derivatives and furan derivatives have stronger fluorescence properties, and the furan derivatives and furan derivatives have different characteristics due to different structures. However, the prior art lacks a semiconductor material having both high electron mobility and high fluorescence.
Accordingly, there is a need for improvements and developments in the art.
Disclosure of Invention
In view of the above-mentioned shortcomings of the prior art, the present invention provides a semiconductor material, a method for preparing the same, and an organic light emitting diode, which aims to solve the problem that the conventional organic semiconductor material cannot achieve both high electron mobility and high fluorescence efficiency.
The technical scheme of the invention is as follows:
the semiconductor material has a molecular structure general formula
Figure BDA0001734521790000021
Wherein Ar1 and Ar2 are both N-containing aromatic groups or aromatic groups substituted by electron-deficient groups.
The semiconductor material, wherein the electron-deficient group comprises a cyano group, a nitro group and a halogen group.
The semiconductor material, wherein the N-containing aromatic group comprises:
Figure BDA0001734521790000022
Figure BDA0001734521790000023
Figure BDA0001734521790000024
wherein, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18 and R19 are independently selected from one of cyano, nitro, alkyl, aryl or nitrogen-containing heterocycle.
The semiconductor material, wherein the semiconductor material comprises:
Figure BDA0001734521790000025
Figure BDA0001734521790000026
Figure BDA0001734521790000031
Figure BDA0001734521790000041
a method of preparing a semiconductor material, comprising the steps of:
mixing benzothiophene and N-bromosuccinimide, and reacting to generate 3-bromobenzothiophene;
mixing the 3-bromobenzothiophene with hydrogen peroxide, and reacting to generate benzothiophene oxide;
mixing the benzothiophene oxide with phenol, and reacting to obtain a compound with a molecular structural formula
Figure BDA0001734521790000042
The first intermediate of (a);
mixing the first intermediate with diisobutyl aluminum hydride, and reacting to obtain the final product with a molecular structural formula
Figure BDA0001734521790000043
A second intermediate of (a);
dissolving the second intermediate in glacial acetic acid, adding N-bromosuccinimide, and mixing to obtain the final product with a molecular structural formula
Figure BDA0001734521790000051
The third intermediate of (4);
reacting the third intermediate with a catalyst PdCl2(PPh3)2Mixing, reacting to obtain the molecular structural formula
Figure BDA0001734521790000052
The fourth intermediate of (1);
mixing the fourth intermediate with liquid bromine, and reacting to obtain a compound with a molecular structural formula
Figure BDA0001734521790000053
The fifth intermediate of (4);
mixing the fifth intermediate with one of N-aryl-containing boric acid, N-aryl-tin-containing aromatic boric acid substituted by electron-deficient group or aromatic tin substituted by electron-deficient group, and passing through PdCl2(PPh3)2The catalyst is catalyzed and coupled to react to obtain the compound with the molecular structural formula
Figure BDA0001734521790000054
Wherein Ar1 and Ar2 are both N-containing aromatic groups or electron-deficient group-substituted aromatic groups.
The organic light-emitting diode comprises an electronic function layer, wherein the electronic function layer is prepared from the semiconductor material.
The organic light emitting diode, wherein the electronic function layer is an electron injection layer and/or an electron transport layer.
Has the advantages that: the invention designs a semiconductor material simultaneously containing thiophene functional groups and furan functional groups by combining the characteristics that thiophene derivatives have higher electron mobility and furan derivatives have higher fluorescence performance, and the molecular structural general formula of the semiconductor material is
Figure BDA0001734521790000055
Wherein Ar1 and Ar2 are both N-containing aromatic groups or electron-deficient group-substituted aromatic groups, and the electron-deficient functional groups are introduced into Ar1 and Ar2 to further obtain [1]]Benzothiophene [3,2-b ]][1]Electron transport capability and luminous efficiency of benzofuran. The invention can effectively solve the problem that the existing semiconductor material has poor high electron mobility and high fluorescence efficiency.
Detailed Description
The present invention provides a semiconductor material, a method for preparing the same, and an organic light emitting diode, and the present invention is described in further detail below in order to make the objects, technical solutions, and effects of the present invention clearer and clearer. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In order to solve the problem that the existing semiconductor material cannot achieve both high electron mobility and high fluorescence efficiency, the invention provides a semiconductor material, wherein the general formula of the molecular structure of the semiconductor material is
Figure BDA0001734521790000061
Wherein, Ar1 and Ar2 are both N-containing aromatic groups or electron-deficient group substituted aromatic groups.
Furan rings have been widely used to construct pi-conjugated molecules, furan derivatives have the advantages of (1) substitution of the sulfur atom with oxygen reduces aromaticity on the one hand, the molecule has more quinoid structural features, allowing better delocalization of pi-electrons; on the other hand, the oxidation potential can be lowered, so that the HOMO orbital energy level is increased, and therefore, the injection and the transmission of holes are facilitated. (2) Thiophene contains relatively heavy sulfur atoms, and the heavy atoms generate spin-orbit coupling to generate internal conversion, so that fluorescence quenching is caused, furan semiconductors have no problem of fluorescence quenching caused by spin-orbit coupling, and compared with thiophene semiconductors, the furan semiconductors have more excellent fluorescence properties, so that the thiophene semiconductors can be used for preparing organic semiconductor light-emitting devices, including OLEDs and organic light-emitting transistors (OLETs). (3) Furan compounds have less aromaticity and less intermolecular π - π interaction, so that solubility is relatively high. (4) Furan is a biodegradable material that can be prepared from biorenewable raw materials, which makes it more suitable for large-scale applications.
The invention combines the characteristics of thiophene derivatives having higher electron mobility and furan derivatives having higher fluorescence performance, designs a semiconductor material simultaneously containing thiophene functional groups and furan functional groups, wherein the name of the semiconductor material is [1] benzothiophene [3,2-b ] [1] benzofuran derivatives, Ar1 and Ar2 combined on the [1] benzothiophene [3,2-b ] [1] benzofuran are N-containing aromatic groups or electron-deficient group substituted aromatic groups, and the N-containing aromatic groups or the electron-deficient group substituted aromatic groups can promote the [1] benzothiophene [3,2-b ] [1] benzofuran to have higher electron mobility and luminous efficiency due to the introduction of the electron-deficient functional groups, so the semiconductor material provided by the invention can be used as an electron functional layer of an organic light-emitting diode device, and preparing the semiconductor material into a semiconductor film by a vacuum evaporation coating or a spin coating method, and further preparing the organic light-emitting diode device with high electron mobility and high fluorescence efficiency.
Specifically, the semiconductor material provided by the invention is bilaterally substituted [1]]Benzothiophene [3,2-b ]][1]Benzofuran derivatives, said bilateral substitution [1]Benzothiophene [3,2-b ]][1]The molecular structure general formula of the benzofuran derivative is
Figure BDA0001734521790000071
Wherein, Ar1 and Ar2 are both N-containing aromatic groups or electron-deficient group substituted aromatic groups, and Ar1 and Ar2 can be the same group or different groups.
Preferably, the electron deficient groups include cyano, nitro and halo groups.
More preferably, in the semiconductor material, the N-containing aromatic group includes:
Figure BDA0001734521790000072
Figure BDA0001734521790000073
Figure BDA0001734521790000074
wherein, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18 and R19 are independently selected from one of cyano, nitro, alkyl, aryl or nitrogen-containing heterocycle.
By way of example, the molecular structural formula of the semiconductor material provided by the invention specifically includes:
Figure BDA0001734521790000075
Figure BDA0001734521790000081
Figure BDA0001734521790000091
further, the present inventionThe invention also provides a molecular structure general formula as
Figure BDA0001734521790000092
The preparation method of the semiconductor material comprises the following steps:
mixing benzothiophene and N-bromosuccinimide, and reacting to generate 3-bromobenzothiophene;
mixing the 3-bromobenzothiophene with hydrogen peroxide, and reacting to generate benzothiophene oxide;
mixing the benzothiophene oxide with phenol to react to generate a compound with a molecular structural formula of
Figure BDA0001734521790000101
The first intermediate of (1);
mixing the first intermediate with diisobutyl aluminum hydride, and reacting to obtain the final product with a molecular structural formula
Figure BDA0001734521790000102
A second intermediate of (a);
dissolving the second intermediate in glacial acetic acid, adding N-bromosuccinimide, and mixing to obtain the final product with a molecular structural formula
Figure BDA0001734521790000103
The third intermediate of (4);
reacting the third intermediate with a catalyst PdCl2(PPh3)2Mixing, reacting to obtain the molecular structural formula
Figure BDA0001734521790000104
A fourth intermediate of (4);
mixing the fourth intermediate with liquid bromine, and reacting to obtain a compound with a molecular structural formula of
Figure BDA0001734521790000105
The fifth intermediate of (4);
mixing the fifth intermediate with N-containing arylboronic acid, N-containing aryltin, electron-deficient group-substituted arylboronic acid or electron-deficient groupOne of the substituted aromatic tin is mixed and passed through PdCl2(PPh3)2The catalyst is catalyzed, coupled and reacted to obtain the molecular structural formula
Figure BDA0001734521790000106
The semiconductor material of (1), wherein each of Ar1 and Ar2 is Ar1 and Ar2 is an N-containing aromatic group or an electron-deficient group-substituted aromatic group.
Furthermore, the invention also provides an organic light-emitting diode which comprises an electronic function layer, wherein the electronic function layer is prepared by adopting the semiconductor material. In particular, the electron functional layer is an electron injection layer and/or an electron transport layer.
The following further illustrates a method for producing a semiconductor material according to the present invention by way of specific examples:
example 1
2, 7-bis (pyridin-2-yl) [1]]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran is as follows:
Figure BDA0001734521790000111
the preparation method comprises the following specific steps:
20g (150mmol) of benzothiophene are dissolved in 150mL of chloroform and 33.2g (186mmol) of N-bromosuccinimide are added portionwise at 0 ℃ and, after the addition, after 4h of reaction at 0 ℃ the mixture is allowed to warm to room temperature and stirred for a further 24 h. Adding 60mL of chloroform, washing with a sodium thiosulfate aqueous solution, saturated sodium carbonate and water respectively, drying an organic phase with anhydrous magnesium sulfate, concentrating, and carrying out column chromatography to obtain the 3-bromobenzothiophene.
Dissolving 10g (46mmol) of 3-bromobenzothiophene in 80mL of dichloromethane and 80mL of trifluoroacetic acid solution, stirring for 5 minutes at room temperature, adding 4mL of 35% hydrogen peroxide, stirring until the raw materials completely react, neutralizing with saturated sodium carbonate solution to be neutral, separating liquid, washing an organic phase with saturated sodium bicarbonate and water, drying over anhydrous magnesium sulfate, concentrating, and carrying out column chromatography to obtain a compound 3-bromobenzothiophene-1-oxygen.
2.3g (10mmol) of 3-bromobenzothiophene-1-oxide, 3.4g (20mmol) of phenol, 2.76g (20mmol) of potassium carbonate and 30mL of anhydrous DMF are stirred at 70 ℃ for reaction overnight, the reaction mixture is cooled to room temperature and concentrated, the residue is dissolved in 50mL of dichloromethane, the solution is washed with saturated brine and water, the organic phase is dried over anhydrous magnesium sulfate, the concentration is carried out, and the 3-phenoxybenzothiophene-1-oxide is obtained by column chromatography.
Dissolving 2.54g (8mmol) of 3-phenoxybenzothiophene-1-oxygen in 50mL of anhydrous toluene, slowly dropwise adding diisobutylaluminum hydride (16mmol,13mL and 20% toluene solution) at 0 ℃, stirring at 65 ℃ after adding, reacting until the raw material disappears, cooling to 0 ℃, neutralizing with 2M sodium hydroxide aqueous solution, extracting with dichloromethane for three times, combining organic phases, washing the organic phases with water to the center, drying with anhydrous magnesium sulfate, concentrating, and carrying out column chromatography to obtain the 3-phenoxybenzothiophene.
1.82g.6(6mmol) of 3-phenoxybenzothiophene was dissolved in 30mL of glacial acetic acid, 1.2g (6.6mmol) of NBS was added, stirring was carried out for 10 minutes, and the reaction was continued at 55 ℃ with stirring for 2 h. Cooling to room temperature, adding 80mL of ice water, extracting with ethyl acetate for three times, combining organic phases, washing the organic phases with saturated sodium carbonate, saturated brine and water, drying over anhydrous magnesium sulfate, and carrying out column chromatography to obtain the 2-bromo-3-phenoxybenzothiophene.
1.51g (4mmol) of 2-bromo-3-phenoxybenzothiophene and 0.67g (8mmol) of sodium acetate were dissolved in 80ml of N, N-dimethylacetamide, and 0.14g (0.2mmol) of PdCl were added under nitrogen2(PPh3)2Stirring overnight at 140 deg.C, cooling to room temperature, adding 200mL of 1mol/L hydrochloric acid, extracting with 500mL of ethyl acetate and n-hexane (volume ratio 1:1), washing the organic phase with saturated saline and water, drying over anhydrous magnesium sulfate, concentrating, and performing column chromatography to obtain target compound [ 1%]Benzothiophene [3,2-b ]][1]A benzofuran.
4.48g,20mmol of [1] benzothiophene [3,2-b ] [1] benzofuran were dissolved in 250mL of chloroform at 0 ℃ in 100mL of chloroform solution containing 9.6g, 60mmol of liquid bromine, a chloroform solution of liquid bromine was added dropwise until the reaction of the starting material was completed, and saturated aqueous sodium thiosulfate solution was added to reduce excess liquid bromine. Washing the organic phase with saturated sodium bicarbonate water solution, drying, and chromatographic separation with petroleum ether as eluent to obtain 2, 7-dibromo 1 benzothiophene 3,2-b 1 benzofuran.
Will be 2.0g (5mmol)2, 7-dibromo [1]]Benzothiophene [3,2-b ]][1]Benzofuran and 1.84g (15mmol,3 equivalents) of pyridine-2-boronic acid are dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate are added, nitrogen is used for 30min, and Pd (PPh) is added3)4(2% equiv.) stirred at 110C under nitrogen for 24h, the reaction mixture poured into 100mL of methanol, filtered, and the solid washed with hydrochloric acid and water. Obtaining 2, 7-di (pyridine-2-yl) [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 2
2, 7-bis (pyridin-3-yl) [1]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran comprises the following steps:
Figure BDA0001734521790000121
the preparation method comprises the following specific steps:
the same procedure as in example 1 was used to prepare 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
2.0g (5mmol) of 2, 7-dibromo [1] are reacted]Benzothiophene [3,2-b ]][1]Benzothiophene and 1.84g (15mmol,3 equivalents) of pyridine-3-boronic acid were dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate solution was added, nitrogen was used for 30min, and Pd (PPh) was added3)4(2% equiv.) and stirred at 110C under nitrogen for 24h, the reaction mixture was poured into 100mL of methanol, filtered, and the solid was washed with hydrochloric acid and water. Obtaining 2, 7-di (pyridine-3-yl) [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 3
2, 7-bis (pyridin-4-yl) [1]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran is as follows:
Figure BDA0001734521790000131
the preparation method comprises the following specific steps:
the same procedure was followed as in example 1 to prepare 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
2.0g (5mmol) of 2, 7-dibromo [1] are reacted]Benzothiophene [3,2-b ]][1]Benzofuran and 1.84g (15mmol,3 equivalents) of pyridine-4-boronic acid are dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate are added, nitrogen is used for 30min, andPd(PPh3)4(2% equiv.) stirred at 110C under nitrogen for 24h, the reaction mixture poured into 100mL of methanol, filtered, and the solid washed with hydrochloric acid and water. Obtaining 2, 7-di (pyridine-4-yl) [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 4
2, 7-bis (quinolin-3-yl) [1]]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran comprises the following steps:
Figure BDA0001734521790000132
the preparation method comprises the following specific steps:
the same procedure was followed as in example 1 to prepare 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
2.0g (5mmol) of 2, 7-dibromo [1] are reacted]Benzothiophene [3,2-b ]][1]Benzofuran and 2.60g (15mmol,3 equiv.) of quinoline-3-boronic acid were dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate solution was added, nitrogen was used for 30min, and Pd (PPh) was added3)4(2% equiv.) and stirred at 110C under nitrogen for 24h, the reaction mixture was poured into 100mL of methanol, filtered, and the solid was washed with hydrochloric acid and water. Obtaining 2, 7-di (quinoline-3-yl) [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 5
2, 7-bis (quinolin-8-yl) [1]]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran comprises the following steps:
Figure BDA0001734521790000141
the preparation method comprises the following specific steps:
the same procedure was followed as in example 1 to prepare 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
2.0g (5mmol) of 2, 7-dibromo [1] are reacted]Benzothiophene [3,2-b ]][1]Benzofuran and 2.60g (15mmol,3 equiv.) of quinoline-8-boronic acid were dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate solution was added, nitrogen was used for 30min, and Pd (PPh) was added3)4(2% equiv.) stirred at 110C under nitrogen for 24h, the reaction mixture poured into 100mL of methanol, filtered, and the solid washed with hydrochloric acid and water. By sublimation under high vacuumTo obtain 2, 7-di (quinolin-8-yl) [1]]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 6
2, 7-bis (1, 10-phenanthroline-3-yl) -4-yl [1]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran is as follows:
Figure BDA0001734521790000151
the preparation method comprises the following specific steps:
the same procedure was followed as in example 1 to prepare 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
2.0g (5mmol) of 2, 7-dibromo [1] are reacted]Benzothiophene [3,2-b ]][1]Benzofuran and 3.36g (15mmol,3 equivalents) of 1, 10-phenanthroline-3-boronic acid are dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate solution are added, nitrogen is used for blowing and sucking for 30min, and Pd (PPh) is added3)4(2% equiv.) and stirred at 110C under nitrogen for 24h, the reaction mixture was poured into 100mL of methanol, filtered, and the solid was washed with hydrochloric acid and water. Obtaining 2, 7-di (1, 10-o-phenanthroline-3-yl) -4-yl [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 7
The synthetic process of the 2, 7-di-benzothiazole-4-yl [1] benzothiophene [3,2-b ] [1] benzofuran comprises the following steps:
Figure BDA0001734521790000152
the preparation method comprises the following specific steps:
the same procedure as in example 1 was used to prepare 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran;
dissolving 2, 7-dibromo [1] benzothiophene [3,2-b ] [1] benzofuran (3.8g,10mmol), dipinacol borate (7.62g,30mmol), potassium acetate (3.92g,40mmol) and [1, 1' -bis (diphenylphosphino) ferrocene ] palladium (II) dichloride dichloromethane complex (0.3mmol, 0.25g) in 100mL dimethyl sulfoxide under nitrogen protection, purging with nitrogen for 15 minutes, heating at 80 ℃ for 10 hours, cooling to room temperature, pouring into ice water, extracting with dichloromethane three times, combining the organic phases, washing the organic phases with water three times, drying with magnesium sulfate, concentrating, and purifying by column chromatography to obtain 2, 7-dipinacoloboronate [1] benzothiophene [3,2-b ] [1] benzofuran;
2.38g (5mmol) of 2, 7-dipinacolobonato [1]]Benzothiophene [3,2-b ]][1]Benzofuran and 3.23g (15mmol,3 equiv.) of 4-bromobenzothiadiazole are dissolved in 50mL toluene, 10mL of 2M aqueous potassium carbonate are added, nitrogen is purged for 30min, and Pd (PPh) is added3)4(2% equiv.) stirred at 110C under nitrogen for 24h, the reaction mixture poured into 100mL of methanol, filtered, and the solid washed with hydrochloric acid and water. Obtaining 2, 7-bis-benzothiazol-4-yl [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 8
2, 7-Dibenzothiazol-5-yl [1]]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran comprises the following steps:
Figure BDA0001734521790000161
the preparation method comprises the following specific steps:
the same procedure was followed as in example 7 to prepare 2, 7-dipinaconoboronate [1] benzothiophene [3,2-b ] [1] benzofuran;
2.38g (5mmol) of 2, 7-dipinacolobonato [1]]Benzothiophene [3,2-b ]][1]Benzofuran and 3.23g (15mmol,3 equiv.) of 5-bromobenzothiadiazole were dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate solution was added, nitrogen was used for bubbling for 30min, and Pd (PPh) was added3)4(2% equiv.) stirred at 110C under nitrogen for 24h, the reaction mixture poured into 100mL of methanol, filtered, and the solid washed with hydrochloric acid and water. Obtaining 2, 7-di-benzothiazole-5-yl [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 9
2, 7-bis- (2, 4-diphenyl-1, 3, 5-triazin-6-yl) [1]Benzothiophene [3,2-b ]][1]The synthetic process of benzofuran is as follows:
Figure BDA0001734521790000171
the preparation method comprises the following specific steps:
the same procedure was followed as in example 7 to prepare 2, 7-dipinaconoboronate [1] benzothiophene [3,2-b ] [1] benzofuran;
2.38g (5mmol) of 2, 7-dipinacolobonate [1]]Benzothiophene [3,2-b ]][1]Benzofuran and 4.00g (15mmol,3 equivalents) of 2, 4-diphenyl-6-chloro-1, 3, 5-triazine are dissolved in 50mL of toluene, 10mL of 2M aqueous potassium carbonate solution are added, nitrogen is used for 30min, and Pd (PPh) is added3)4(2% equiv.) stirred at 110C under nitrogen for 24h, the reaction mixture poured into 100mL of methanol, filtered, and the solid washed with hydrochloric acid and water. Obtaining 2, 7-di-benzothiazole-5-yl [1] by high vacuum sublimation]Benzothiophene [3,2-b ]][1]A benzofuran.
Example 10
Preparing a device and testing the performance:
and masking the silicon wafer by using a semiconductor mask, selecting a proper substrate temperature, and preparing a film under high vacuum. And controlling the evaporation rate of the semiconductor material, and carrying out evaporation of an electrode by using an electrode mask after the film is prepared, wherein the electrode material is Au. And testing the performance of the prepared organic light-emitting diode device by using a semiconductor analyzer. Testing Id-Vg and Id-Vd curves using the following formula Id＝(W/2L)μTFTCi(Vg-Vth)2The calculation of the mobility was performed.
The same organic thin film transistor devices were prepared using the conventional materials DPh-BTBT and the semiconductor materials prepared in the embodiments 1, 4, 6 and 9 of the present invention, respectively, and the electron mobility and the fluorescence quantum efficiency were respectively tested, and the results are shown below:
Figure BDA0001734521790000172
Figure BDA0001734521790000181
from the above experimental results, it can be seen that the semiconductor material prepared by the present invention is similar to the existing semiconductor material
Figure BDA0001734521790000182
The (DPh-BTBT) material has higher electron mobility, but the material provided by the invention has higher fluorescence efficiency compared with the existing DPh-BTBT material.
In summary, the invention designs a semiconductor material containing both thiophene functional groups and furan functional groups by combining the characteristics that thiophene derivatives have higher electron mobility and furan derivatives have higher fluorescence performance, and the molecular structural general formula of the semiconductor material is
Figure BDA0001734521790000183
Wherein, Ar1 and Ar2 are both N-containing aromatic groups or electron-deficient group substituted aromatic groups, and Ar1 and Ar2 can further [1] due to the introduction of electron-deficient functional groups]Benzothiophene [3,2-b ]][1]Electron transport capability and luminous efficiency of benzofuran. The invention can effectively solve the problem that the existing semiconductor material has poor high electron mobility and high fluorescence efficiency.
It is to be understood that the invention is not limited in its application to the details of the examples set forth above, but that modifications and variations may be effected therein by those of ordinary skill in the art in light of the above teachings, and that all such modifications and variations are intended to be within the purview of the appended claims.

Claims (5)

1. The semiconductor material is characterized in that the general molecular structural formula of the semiconductor material is
Figure FDA0003619768600000011
Wherein Ar1 and Ar2 are both N-containing aromatic groups or aromatic groups substituted by electron-deficient groups; the electron-deficient group is one of cyano, nitro and halogen, and the N-containing aromatic group is
Figure FDA0003619768600000012
Figure FDA0003619768600000013
Figure FDA0003619768600000014
Wherein, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18 and R19 are independently selected from one of cyano-group, nitro-group, alkyl-group, aryl-group or nitrogen-containing heterocycle.
2. The semiconductor material of claim 1, wherein the semiconductor material is
Figure FDA0003619768600000015
Figure FDA0003619768600000016
Figure FDA0003619768600000021
Figure FDA0003619768600000022
One kind of (1).
3. A method for preparing a semiconductor material, comprising the steps of:
mixing benzothiophene and N-bromosuccinimide, and reacting to generate 3-bromobenzothiophene;
mixing the 3-bromobenzothiophene with hydrogen peroxide, and reacting to generate benzothiophene oxide;
mixing the benzothiophene oxide with phenol to react to generate a compound with a molecular structural formula of
Figure FDA0003619768600000023
The first intermediate of (a);
reacting the first intermediate with diisobutylhydrogenMixing aluminum oxide, reacting to generate a molecular structural formula
Figure FDA0003619768600000024
A second intermediate of (a);
dissolving the second intermediate in glacial acetic acid, adding N-bromosuccinimide, and mixing to obtain the final product with a molecular structural formula
Figure FDA0003619768600000025
A third intermediate of (4);
reacting the third intermediate with a catalyst PdCl2(PPh3)2Mixing, reacting to obtain the compound with the molecular structural formula
Figure FDA0003619768600000026
The fourth intermediate of (1);
mixing the fourth intermediate with liquid bromine, and reacting to obtain a compound with a molecular structural formula
Figure FDA0003619768600000027
The fifth intermediate of (4);
mixing the fifth intermediate with one of N-aryl-containing boric acid, N-aryl-tin-containing aromatic boric acid substituted by electron-deficient group or aromatic tin substituted by electron-deficient group, and passing through PdCl2(PPh3)2The catalyst is catalyzed, coupled and reacted to obtain the molecular structural formula
Figure FDA0003619768600000031
Wherein Ar1 and Ar2 are both N-containing aromatic groups or electron-deficient group-substituted aromatic groups.
4. An organic light emitting diode comprising an electronic functional layer, wherein the electronic functional layer is prepared from the semiconductor material according to any one of claims 1 to 2.
5. The OLED of claim 4, wherein the electron functional layer is an electron injection layer and/or an electron transport layer.
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