CN113372333B - Optical material containing phenanthroimidazole structure, preparation method and application - Google Patents
Optical material containing phenanthroimidazole structure, preparation method and application Download PDFInfo
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Abstract
The invention provides an optical material containing a phenanthroimidazole structure, a preparation method and application thereof, wherein the optical material containing the phenanthroimidazole structure utilizes the efficient fluorescence quantum efficiency characteristic of anthracene as a bridge, and the electron donating property of the phenanthroimidazole electron-withdrawing carbazole group is utilized to ensure that the carrier injection and the carrier transmission are more balanced, thereby being beneficial to improving the device performance; meanwhile, the fluorescent quantum efficiency of the solid film aggregation state is improved, and the high-efficiency blue light emission can be carried out in an organic solvent. The optical material containing the phenanthroimidazole structure is used as a luminescent layer material to manufacture the organic luminescent semiconductor device, so that the luminescent efficiency and the luminescent brightness of the organic luminescent semiconductor device can be improved, and the structural formula of the material is shown as formula I:
Description
Technical Field
The invention belongs to the technical field of photoelectric materials, relates to an optical material containing a phenanthroimidazole structure, and in particular relates to an optical material containing a phenanthroimidazole structure, a preparation method and application thereof.
Background
Road traffic safety has been the most important issue for vehicle owners and traffic management, where hidden hazards caused by low visibility traffic environments (low visibility weather conditions such as rain, snow, heavy fog, haze, etc.) are evident. When the vehicle runs at night or under low-visibility weather conditions and no light-gathering object or reference object exists at the two sides of the road, the light is easy to scatter, the light becomes dark, and the visibility becomes low.
Because of the problem of the visible angle or brightness of the road sign, the road guiding sign is not easy to identify or lose efficacy at night and in low-visibility weather conditions, and traffic accidents are very easy to occur. According to the 2019 Chinese urban traffic report, traffic accidents occur in 100 main cities in the whole country during the peak period of working days, wherein the traffic accidents caused by low visual visibility exceed 20 percent. In order to ensure the safety and smooth traffic of drivers, it is important to develop a set of road arrow and two side line devices which can be used at night and with low visibility.
After passing current, the filament of the traditional incandescent lamp emits light by heating, most of energy is converted into heat, and the heat is lost by heat radiation, so that huge energy waste is caused; the more emerging fluorescent lamp has mercury hazard and ultraviolet hazard, which seriously affects the environmental safety and the use safety; LEDs are prone to fatigue. With the development of lighting technology, in recent years, organic light emitting semiconductor (Organic Electroluminescence Display, OLED) technology is becoming more and more important and accepted as an emerging technology.
The light emitting principle of the OLED is that an organic semiconductor optical material is driven by an electric field to form excitons by carrier injection, transmission, electron and hole combination, and then the phenomenon of light emission is caused by radiative recombination. As an emerging light source, the OLED has the advantages of high color rendering index, ultra-thin property, transparency, flexibility, cold light source, no ultraviolet, no infrared, no glare and the like. With global importance on green energy and environmental protection, the unique light source characteristics of the OLED can effectively reduce energy loss, and the environment-friendly and efficient light source can be well applied and can push green energy. However, in the conventional OLED technology, there are a series of problems such as insufficient balance between carrier injection and transport, low fluorescence quantum efficiency in the solid thin film aggregation state, and the like, which need to be solved.
Disclosure of Invention
Aiming at the defects and shortcomings in the prior art, the invention aims to provide an optical material containing a phenanthroimidazole structure, a preparation method and application thereof, and solves the technical problem of low aggregation state fluorescence quantum efficiency of a solid film of the existing organic semiconductor optical material.
In order to solve the technical problems, the invention adopts the following technical scheme:
an optical material containing phenanthroimidazole structure, which is characterized in that the structural formula of the material is shown as formula I:
the invention also has the following technical characteristics:
the invention also provides a preparation method of the optical material containing the phenanthroimidazole structure, which comprises the following steps: a method for preparing an optical material containing a phenanthroimidazole structure as claimed in claim 1, comprising the steps of:
dissolving 4-bromobenzaldehyde, 4-tertiary butyl aniline and 9, 10-phenanthrenequinone in an acetic acid-ammonium acetate buffer solution, heating, stirring and mixing to react at the reaction temperature of 115-125 ℃ for 2-4 hours to obtain a crude product of 4-bromophenanthroimidazole, and sequentially washing the crude product of 4-bromophenanthroimidazole with methanol, filtering, separating, vacuum drying and purifying by column chromatography to obtain a purified product of 4-bromophenanthroimidazole;
adding 9-naphthyl anthracene boric acid, 3-bromocarbazole and catalyst tetra-triphenylphosphine palladium into a clean two-necked flask, adding toluene and saturated potassium carbonate aqueous solution in a dry nitrogen atmosphere, carrying out reflux reaction to obtain a crude product of 9-naphthyl-10-carbazolyl anthracene, and sequentially extracting, distilling under reduced pressure and purifying by column chromatography to obtain a purified product of 9-naphthyl-10-carbazolyl anthracene;
step three, adding the 4-bromophenanthroimidazole obtained in the step one, the 9-naphthyl-10-carbazolyl anthracene obtained in the step two, palladium acetate serving as a catalyst, tri-tertiary butyl phosphine and potassium tert-butoxide into a clean two-necked flask, adding toluene in a dry nitrogen atmosphere, carrying out reflux reaction to obtain a crude product of a target product 8, and sequentially extracting, distilling under reduced pressure and purifying by column chromatography the crude product of the target product 8 to obtain a purified product of the target product 8;
wherein, the structural formula of the 4-bromobenzaldehyde is as follows:
the structural formula of the 4-tertiary butyl aniline is as follows:
the structural formula of the 9, 10-phenanthrenequinone is as follows:
the structural formula of the 4-bromophenanthroimidazole is as follows:
the structural formula of the 9-naphthyl anthracene boric acid is as follows:
the structural formula of the 3-bromocarbazole is as follows:
the structural formula of the 9-naphthyl 10-carbazolyl anthracene is as follows:
the target product 8 is the optical material containing phenanthroimidazole structure as in claim 1.
Specifically, in the first step, the molar amount of the 9, 10-phenanthrenequinone is 0.5-2 times of the molar amount of the 4-bromobenzaldehyde; the molar quantity of the 4-tertiary butyl aniline is 0.3 to 1 time of that of the 4-bromobenzaldehyde.
Preferably, in the first step, the molar amount of the 9, 10-phenanthrenequinone is 1 time of the molar amount of the 4-bromobenzaldehyde; the molar quantity of the 4-tertiary butyl aniline is 1 time of that of the 4-bromobenzaldehyde; the temperature of stirring and mixing is 120 ℃, and the time of stirring and mixing is 3 hours.
Specifically, in the second step, the molar amount of the 3-bromocarbazole is 0.5-2 times of that of the 9-naphthyl anthracene boric acid; the molar quantity of the tetraphenylphosphine palladium is 0.025-0.1 time of that of the 9-naphthyl anthracene boric acid; the volume ratio of toluene to saturated aqueous potassium carbonate solution is 4:1; the reaction temperature range of the reflux reaction is 90-120 ℃ and the reaction time is 12-24 h.
Preferably, in the second step, the molar amount of the 3-bromocarbazole is 1.2 times of the molar amount of the 9-naphthylanthracene boric acid; the molar quantity of the tetraphenylphosphine palladium is 0.05 times of that of the 9-naphthyl anthracene boric acid; the reaction temperature of the reflux reaction is 90 ℃ and the reaction time is 12 hours.
Specifically, in the third step, the molar amount of the 9-naphthyl-10-carbazolyl anthracene is 0.5-2 times of the molar amount of the 4-bromophenanthroimidazole; the molar quantity of the palladium acetate is 0.015-0.05 times of the molar quantity of the 4-bromophenanthroimidazole; the molar quantity of the tri-tert-butyl phosphine is 0.025-0.05 times of the molar quantity of the 4-bromophenanthroimidazole; the molar quantity of the potassium tert-butoxide is 1-4 times of that of the 4-bromophenanthroimidazole; the reaction temperature range of the reflux reaction is 95-120 ℃ and the reaction time is 24-36 h.
Preferably, in the third step, the molar amount of the 9-naphthyl-10-carbazolyl anthracene is 1 time of the molar amount of the 4-bromophenanthroimidazole; the molar quantity of the palladium acetate is 0.05 times of that of the 4-bromophenanthroimidazole; the molar quantity of the tri-tert-butyl phosphine is 0.05 times of that of the 4-bromophenanthroimidazole; the molar quantity of the potassium tert-butoxide is 1.5 times of that of the 4-bromophenanthroimidazole; the reaction temperature of the reflux reaction is 110 ℃, and the reaction time is 24 hours.
The optical material containing the phenanthroimidazole structure is applied to the preparation of the luminescent layer material in the organic luminescent semiconductor device.
For the application described above, the organic light-emitting semiconductor device is a road light-emitting guidance device.
Compared with the prior art, the invention has the beneficial technical effects that:
according to the optical material containing the phenanthroimidazole structure, provided by the invention, by utilizing the efficient fluorescence quantum efficiency characteristic of anthracene as a bridge and by means of the electron donating property of the phenanthroimidazole electron-withdrawing carbazole group, carrier injection and transmission are more balanced, and the performance of a device is improved; meanwhile, the fluorescent quantum efficiency of the solid film aggregation state is improved, and the high-efficiency blue light emission can be carried out in an organic solvent.
And (II) the optical material containing the phenanthroimidazole structure is used as a luminescent layer material in the organic light-emitting semiconductor equipment, so that the luminescent efficiency and the luminescent brightness of the organic light-emitting semiconductor equipment can be improved, and the guided vehicle can be ensured to stably and safely run under the environment of low visibility or darkness of the organic light-emitting semiconductor equipment.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of the target product 8 of the example.
Fig. 2 is a nuclear magnetic resonance spectrum of the target product 8 of the example.
Fig. 3 is a mass spectrum of the target product 8 of the example.
FIG. 4 is an absorption spectrum of a methylene chloride solution of the target product 8 of example.
Fig. 5 is an emission spectrum of a dichloromethane solution of the target product 8 of example.
FIG. 6 is an absorption spectrum of the target product 8 film of the example in an aggregated state.
FIG. 7 is an emission spectrum of the target product 8 film of the example in an aggregated state.
FIG. 8 is a thermogram of the target product 8 of the example.
The technical scheme of the invention is further described below with reference to the accompanying drawings and examples.
Detailed Description
The synthetic route of the target product 8 of the invention is as follows:
in the invention, the following components are added:
the UV-visible spectrophotometer model was UV-2700, available from Shimadzu corporation.
The fluorescence spectrometer was model number FLS980, available from Edinburgh, UK (Edinburgh Instruments).
The model of the high temperature synchronous thermal analyzer was STA409PC, available from the German Instrument manufacturing company, inc.
The following specific embodiments of the present invention are given according to the above technical solutions, and it should be noted that the present invention is not limited to the following specific embodiments, and all equivalent changes made on the basis of the technical solutions of the present application fall within the protection scope of the present invention.
Examples:
following the above technical scheme, this example gives an optical material containing a phenanthroimidazole structure, denoted as a target product 8, and the structural formula of the target product 8 is as follows:
the preparation method of the target product 8 in this embodiment includes the following steps:
dissolving 10mmoL of 4-bromobenzaldehyde, 10mmoL of 4-tertiary butyl aniline and 10mmoL of 9, 10-phenanthrenequinone into an acetic acid-ammonium acetate buffer solution, stirring and mixing for 2 hours at 120 ℃, uniformly mixing to obtain a crude product of 4-bromophenanthroimidazole, and sequentially performing methanol washing, filtering separation, vacuum drying and column chromatography purification on the crude product of 4-bromophenanthroimidazole to obtain a purified product of 4-bromophenanthroimidazole.
In the first step of this example, the preparation process of the acetic acid-ammonium acetate buffer solution comprises adding 60mmoL of ammonium acetate into 60ml of glacial acetic acid, stirring and mixing uniformly; during column chromatography purification, the stationary phase adopted is silica gel powder, the eluent adopted is petroleum ether and dichloromethane, and the volume ratio of petroleum ether to dichloromethane is 1: the final yield of 2, 4-bromophenanthroimidazole was 75.5%.
Adding 5mmoL of 9-naphthyl anthracene boric acid, 6mmoL of 3-bromocarbazole and 0.25mmoL of catalyst tetra-triphenylphosphine palladium into a clean two-necked flask, adding 40mL of toluene and 10mL of saturated potassium carbonate aqueous solution in a dry nitrogen atmosphere, carrying out reflux reaction at 90 ℃ for 12h to obtain a crude product of 9-naphthyl-10-carbazolyl anthracene, and sequentially extracting, decompressing, distilling and purifying the crude product of 9-naphthyl-10-carbazolyl anthracene to obtain a purified product of 9-naphthyl-10-carbazolyl anthracene.
In the second step of this embodiment, the solvent used in the extraction is a mixed solution of saturated saline and dichloromethane; during column chromatography purification, the adopted stationary phase is silica gel powder, the adopted eluent is petroleum ether and dichloromethane, and the volume ratio of petroleum ether to dichloromethane is 2: the final yield of 1, 9-naphthyl-10-carbazolyl anthracene was 51.2%.
Adding 2mmoL of 4-bromophenanthroimidazole, 2mmoL of 9-naphthyl-10-carbazolyl anthracene, 0.1mmoL of catalyst palladium acetate, 0.1mmoL of tri-tert-butylphosphine and 3mmoL of potassium tert-butoxide into a clean two-necked flask, adding 40mL of toluene in a dry nitrogen atmosphere, carrying out reflux reaction at 110 ℃ for 24 hours to obtain a crude product of a target product 8, and sequentially extracting, distilling under reduced pressure and purifying by column chromatography to obtain a purified product of the target product 8.
In step three of this example, the extraction and column chromatography purification were the same as in step two, and the final yield of the target product 8 was 45.3%.
In this embodiment, the structural formula of 4-bromobenzaldehyde is:
the structural formula of the 4-tertiary butyl aniline is as follows:
the structural formula of the 9, 10-phenanthrenequinone is as follows:
the structural formula of the 4-bromophenanthroimidazole is as follows:
the structural formula of the 9-naphthyl anthracene boric acid is as follows:
the structural formula of the 3-bromocarbazole is as follows:
the structural formula of the 9-naphthyl 10-carbazolyl anthracene is as follows:
and (3) structural identification:
the nuclear magnetic hydrogen spectrum of the target product 8 is shown in figure 1.
The nuclear magnetic hydrogen spectrum data of the target product 8 are: 1 H NMR(400MHz,Chloroform-d)δ8.93(d,J＝7.1Hz,1H),8.80(d,J＝8.5Hz,1H),8.74(d,J＝8.3Hz,1H),8.27(s,1H),8.15–8.07(m,2H),8.06–7.99(m,2H),7.98–7.87(m,3H),7.85–7.72(m,5H),7.71–7.42(m,15H),7.38–7.27(m,7H),1.48(s,9H).
the nuclear magnetic carbon spectrum of the target product 8 is shown in figure 2.
The nuclear magnetic carbon spectrum data of the target product 8 are: 13 C NMR(151MHz,Chloroform-d)δ140.87,139.83,137.81,136.78,136.70,133.44,132.77,130.54,130.27,130.11,129.63,129.37,128.52,128.12,127.97,127.91,127.37,127.33,127.02,126.48,126.42,126.38,126.21,125.09,124.99,124.21,123.82,123.56,123.54,123.17,121.04,120.56,110.02,109.70,35.18,31.41.
the mass spectrum of the target product 8 is shown in fig. 3.
The target product 8 prepared in this embodiment is used for preparing a luminescent layer material in an organic luminescent semiconductor device, which is a road luminescent guiding device.
Performance test:
(A) The normalized absorption intensity of the solution of the target product 8 was measured using an ultraviolet-visible spectrophotometer, and the absorption spectrum obtained by the measurement is shown in fig. 4.
(B) The normalized emission intensity of the solution of the target product 8 was measured using a fluorescence spectrometer with an excitation wavelength of 395nm, and the measured fluorescence emission spectrum is shown in fig. 5, with the peak value of the emission peak of the target product 8 appearing at 440 nm.
(C) Measuring the normalized absorption intensity of the target product 8 film by using an ultraviolet-visible spectrophotometer, wherein the measured absorption spectrum is shown in figure 6; in this example, the target product 8 film was prepared by methods conventional in the art.
(D) The normalized emission intensity of the film of the target product 8 is measured by using a fluorescence spectrometer with the excitation wavelength of 390nm, the measured fluorescence emission spectrum is shown in figure 7, and the peak value of the emission peak of the target product 8 appears at 445 nm; in this embodiment, the absolute fluorescence quantum yield of the target product 8 in the thin film can reach 59%, which indicates that the target product 8 can efficiently emit fluorescence in an aggregated state, and has great potential in application of organic light-emitting semiconductor devices.
(E) The target product 8 is subjected to thermogravimetric analysis by using a high-temperature synchronous thermal analyzer, and the specific conditions are that the temperature rising rate is 10K/min, the temperature range is normal temperature to 800 ℃, the protective gas is nitrogen, the structure of the thermogravimetric analysis is shown in fig. 8, and as can be seen from fig. 8, the 5% weight loss temperature of the target product 8 reaches 524 ℃, which indicates that the thermal stability of the target product 8 is excellent, and the method has great potential in preparing high-efficiency excellent organic light-emitting semiconductor equipment.
Claims (10)
1. An optical material containing phenanthroimidazole structure, which is characterized in that the structural formula of the material is shown as formula I:
2. a method for preparing an optical material containing a phenanthroimidazole structure as claimed in claim 1, comprising the steps of:
dissolving 4-bromobenzaldehyde, 4-tertiary butyl aniline and 9, 10-phenanthrenequinone in an acetic acid-ammonium acetate buffer solution, heating, stirring and mixing to react at the reaction temperature of 115-125 ℃ for 2-4 hours to obtain a crude product of 4-bromophenanthroimidazole, and sequentially washing the crude product of 4-bromophenanthroimidazole with methanol, filtering, separating, vacuum drying and purifying by column chromatography to obtain a purified product of 4-bromophenanthroimidazole;
adding 9-naphthyl anthracene boric acid, 3-bromocarbazole and catalyst tetra-triphenylphosphine palladium into a clean two-necked flask, adding toluene and saturated potassium carbonate aqueous solution in a dry nitrogen atmosphere, carrying out reflux reaction to obtain a crude product of 9-naphthyl-10-carbazolyl anthracene, and sequentially extracting, distilling under reduced pressure and purifying by column chromatography to obtain a purified product of 9-naphthyl-10-carbazolyl anthracene;
step three, adding the 4-bromophenanthroimidazole obtained in the step one, the 9-naphthyl-10-carbazolyl anthracene obtained in the step two, palladium acetate serving as a catalyst, tri-tertiary butyl phosphine and potassium tert-butoxide into a clean two-necked flask, adding toluene in a dry nitrogen atmosphere, carrying out reflux reaction to obtain a crude product of a target product 8, and sequentially extracting, distilling under reduced pressure and purifying by column chromatography the crude product of the target product 8 to obtain a purified product of the target product 8;
wherein, the structural formula of the 4-bromobenzaldehyde is as follows:
the structural formula of the 4-tertiary butyl aniline is as follows:
the structural formula of the 9, 10-phenanthrenequinone is as follows:
the structural formula of the 4-bromophenanthroimidazole is as follows:
the structural formula of the 9-naphthyl anthracene boric acid is as follows:
the structural formula of the 3-bromocarbazole is as follows:
the structural formula of the 9-naphthyl 10-carbazolyl anthracene is as follows:
the target product 8 is the optical material containing phenanthroimidazole structure as in claim 1.
3. The method for producing an optical material containing a phenanthroimidazole structure according to claim 2, wherein in the first step, the molar amount of the 9, 10-phenanthroiquinone is 0.5 to 2 times the molar amount of the 4-bromobenzaldehyde; the molar quantity of the 4-tertiary butyl aniline is 0.3 to 1 time of that of the 4-bromobenzaldehyde.
4. The method for producing an optical material having a phenanthroimidazole structure as claimed in claim 3, wherein in the first step, the molar amount of the 9, 10-phenanthroiquinone is 1 time the molar amount of the 4-bromobenzaldehyde; the molar quantity of the 4-tertiary butyl aniline is 1 time of that of the 4-bromobenzaldehyde; the temperature of stirring and mixing is 120 ℃, and the time of stirring and mixing is 3 hours.
5. The method for producing an optical material having a phenanthroimidazole structure according to claim 4, wherein in the second step, the molar amount of 3-bromocarbazole is 0.5 to 2 times the molar amount of 9-naphthylanthracene boric acid; the molar quantity of the tetraphenylphosphine palladium is 0.025-0.1 time of that of the 9-naphthyl anthracene boric acid; the volume ratio of toluene to saturated aqueous potassium carbonate solution is 4:1; the reaction temperature range of the reflux reaction is 90-120 ℃ and the reaction time is 12-24 h.
6. The method for producing an optical material having a phenanthroimidazole structure according to claim 5, wherein in the second step, the molar amount of 3-bromocarbazole is 1.2 times the molar amount of 9-naphthylanthracene boric acid; the molar quantity of the tetraphenylphosphine palladium is 0.05 times of that of the 9-naphthyl anthracene boric acid; the reaction temperature of the reflux reaction is 90 ℃ and the reaction time is 12 hours.
7. The method for producing an optical material having a phenanthroimidazole structure according to claim 6, wherein in the third step, the molar amount of the 9-naphthyl-10-carbazolyl anthracene is 0.5 to 2 times the molar amount of the 4-bromophenanthroimidazole; the molar quantity of the palladium acetate is 0.015-0.05 times of the molar quantity of the 4-bromophenanthroimidazole; the molar quantity of the tri-tert-butyl phosphine is 0.025-0.05 times of the molar quantity of the 4-bromophenanthroimidazole; the molar quantity of the potassium tert-butoxide is 1-4 times of that of the 4-bromophenanthroimidazole; the reaction temperature range of the reflux reaction is 95-120 ℃ and the reaction time is 24-36 h.
8. The method for producing an optical material having a phenanthroimidazole structure according to claim 7, wherein in the third step, the molar amount of the 9-naphthyl-10-carbazolyl anthracene is 1 time the molar amount of the 4-bromophenanthroimidazole; the molar quantity of the palladium acetate is 0.05 times of that of the 4-bromophenanthroimidazole; the molar quantity of the tri-tert-butyl phosphine is 0.05 times of that of the 4-bromophenanthroimidazole; the molar quantity of the potassium tert-butoxide is 1.5 times of that of the 4-bromophenanthroimidazole; the reaction temperature of the reflux reaction is 110 ℃, and the reaction time is 24 hours.
9. Use of an optical material containing a phenanthroimidazole structure as claimed in claim 1 for the preparation of a luminescent layer material in organic light emitting semiconductor devices.
10. The use according to claim 9, wherein the organic light emitting semiconductor device is a road lighting guidance device.
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