CN113072589B - Boron dipyrromethene derivative, preparation method thereof and photoelectric detector using boron dipyrromethene derivative as donor - Google Patents

Boron dipyrromethene derivative, preparation method thereof and photoelectric detector using boron dipyrromethene derivative as donor Download PDF

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CN113072589B
CN113072589B CN202110318492.9A CN202110318492A CN113072589B CN 113072589 B CN113072589 B CN 113072589B CN 202110318492 A CN202110318492 A CN 202110318492A CN 113072589 B CN113072589 B CN 113072589B
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刘淑娟
余波
赵强
陈曦
黄维
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Nanjing University of Posts and Telecommunications
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Abstract

The invention discloses a boron dipyrromethene derivative, a preparation method thereof and a photoelectric detector using the boron dipyrromethene derivative as a donor; alkynyl is introduced into the BODIPY derivative to serve as a P-type semiconductor material and is sensitive to ultraviolet-visible-near infrared light; the bulk heterojunction in the broad-spectrum photoelectric detector comprises a P-type BODIPY derivative and a traditional N-type fullerene material, and meanwhile, a hole transport layer PEDOT is sequentially arranged on one side, located on the anode side of the heterojunction film, of the detector device: PSS, transparent conductive substrate ITO glass, and electron transport layer C arranged on cathode side of the heterojunction film in sequence60An electron buffer layer LiF and a metal back electrode Al. The broad-spectrum photoelectric detector has the advantages of simple device structure and manufacturing process, insensitivity to temperature, high responsivity and high response speed, and has good application value in the fields of photoelectric communication and the like.

Description

Boron dipyrromethene derivative, preparation method thereof and photoelectric detector using boron dipyrromethene derivative as donor
Technical Field
The invention belongs to the field of photoelectron, and relates to a boron dipyrromethene derivative, a preparation method thereof and a photoelectric detector using the boron dipyrromethene derivative as a donor.
Technical Field
In recent years, due to the inherent characteristics of mechanical flexibility, easy processing, good optical sensing performance, biocompatibility and the like, photo detectors (OPDs) have attracted much attention in the fields of digital imaging technology, sensing, communication technology, artificial intelligence and the like. Photodetectors of different wavelength regions play an important role in various optoelectronic technology fields. Therefore, the development of the high-performance visible light photoelectric detector has important significance on the development of science and technology.
The photosensitive materials commonly used in photodetectors include inorganic materials and organic materials, etc., but most inorganic semiconductor materials are disadvantageous for wavelength selectivity due to their wide absorption spectrum from visible to infrared regions. The photoelectric detection has more types of organic materials, and the molecular structure can be flexibly designed to adjust the physical and chemical properties of the materials, thereby well making up for the defects of inorganic materials. The photoelectric separation of charges in the organic material is generated by the dissociation of photogenerated Frenkel charge transfer excitons, and the binding energy range of the photoelectric separation is 0.1-1 eV. Organic materials in photodetection, the low refractive index allows efficient coupling of light into the device, and the typical light absorption length-50 nm allows for ultra-thin photodetection devices. One of the major challenges today is to find organic materials that are strongly light absorbing in the NIR. BODIPY material is one of the most interesting dye compounds in recent years.
The published patent application CN108807683A "a multiplication type organic photodetector with wide spectral response" discloses a multiplication type organic photodetector with wide spectral response, wherein the photosensitive layer is formed by a material containing an organic small molecule donor material (BODIPY material) and an organic small molecule acceptor material (PC)61BM or PC71BM). The donor material (BODIPY) disclosed therein uses Pd (PPh) in the preparation process3)4Firstly, the cost of noble metals such as palladium is high, so that the preparation cost of materials of the BODIPY and derivatives thereof is improved to a certain extent, and the palladium catalyst belongs to hazardous wastes and has high recovery cost, and the environment is also adversely affected by improper treatment; secondly, since palladium catalysts are very sensitive to oxygen, strict requirements are required for controlling oxygen in the preparation process, and the preparation process is complicated.
Disclosure of Invention
The invention aims to provide a boron dipyrromethene derivative, a preparation method thereof and a photoelectric detector using the boron dipyrromethene derivative as a donor; the BODIPY derivative realizes the near-infrared broad-spectrum absorption of the BODIPY derivative by adjusting a substituent at the far end of the BODIPY, realizes the high-matching energy level with a receptor material, and has simpler preparation process and low cost; the photoelectric detector comprises a donor and an acceptor film, and the BODIPY derivative provided by the invention is used as donor doping of an active layer of the device, so that the optical detection rate of the photoelectric detector in a near infrared range is improved, and the preparation cost of the device can be reduced.
The technical scheme of the invention is as follows:
in a first aspect, the present invention provides a class of BODIPY derivatives, wherein molecules of the BODIPY derivatives are any one of the following structural formulas:
Figure BDA0002992231830000021
wherein n is more than or equal to 1;
wherein the compounds BODIPY-DN, BODIPY-TPN and BODIPY-TPP are collectively called BODIPY-X; the compounds Pt-BODIPY-DN, Pt-BODIPY-TPN, and Pt-BODIPY-TPP are collectively referred to as Pt-BODIPY-X hereinafter.
In a second aspect, the invention provides a preparation method of a class of BODIPY derivatives, wherein the synthetic route of the BODIPY derivatives is as follows:
Figure BDA0002992231830000031
wherein, X is any one of Dimethylamino (DN), anilino (TPN) and triphenyl phosphorus (TPP); the preparation process of the BODIPY derivative comprises the following steps: mixing the compound 1 and the acetylbenzyne under the protection of nitrogen; firstly, adding a 10% NaOH solution; adding ethanol until the ethanol is completely dissolved; reacting for a period of time to obtain a compound 2; mixing appropriate amount of compound 2 and appropriate amount of diethylamine, appropriate amount of CH3NO2Sequentially adding the materials into a reaction container, and dissolving the materials by adopting a proper amount of methanol; reacting for a period of time at about 80 ℃ to obtain a compound 3; dissolving a proper amount of the compound 3 and a proper amount of ammonium acetate in n-butanol, reacting at about 70 ℃ to obtain a compound 4, and protecting with nitrogen. Dissolving a proper amount of compound 4 and a proper amount of DIPEA in redistilled dichloromethane, reacting at normal temperature, and then slowly dropwise adding boron trifluoride ethyl ether. Reacting at normal temperature to obtain a compound 5, namely BODIPY-X, and protecting with nitrogen; compound 5, Pt (PBu)3)2Cl2Placing the CuI in a reaction container and protecting with nitrogen; then 10mL of methylene chloride was redistilled. Then throw into the third step of heavy steamingEthylamine and reacting to obtain Pt-BODIPY-X.
In a third aspect, the invention provides a boron dipyrromethene derivative as a donor-doped photodetector, which is sequentially stacked with: the ITO conductive glass layer, the hole transport layer, the active layer, the hole barrier layer, the electron buffer layer and the metal cathode layer;
the hole transport layer is PEDOT: PSS;
the active layer is composed of a Pt-alkynyl BODIPY derivative heterojunction film, the film is formed by mixing a heterojunction donor material and a heterojunction acceptor material, the heterojunction donor material is the BODIPY derivative, and the heterojunction acceptor material is fullerene or any one of fullerene derivatives; the fullerene derivative is C60、C70、PC61BM、PC71Any one of BMs; the thickness of the heterojunction film is 60-150nm, and the heterojunction film is prepared by a spin-coating method.
The hole blocking layer is composed of an electron transport material having a lower HOMO potential;
the electronic buffer layer is composed of LiF;
the metal cathode layer is composed of a metal having a low work function.
Further, the hole transport layer has a PEDOT: the PSS film is formed on an ITO glass substrate by spin coating by a solution method, and the thickness of the film is 20-40 nm.
Further, the hole blocking layer is made of fullerene material C60TPBi and Balq with a film thickness of 8-12nm, or Ca and Mg metal, and is prepared by a vacuum thermal evaporation method.
Furthermore, the thickness of the electronic buffer layer is 1-3nm, and the electronic buffer layer is prepared by a vacuum thermal evaporation method.
Furthermore, the metal cathode layer is an Ag or Al thin film, and is coated on LiF in a vapor deposition mode after being shielded by a mask plate, and the thickness of the film is 80-120 nm.
Furthermore, the transparent substrate is ITO glass, the ITO is a conductive anode, the square resistance of the transparent substrate is 20-30 ohms, and the required ITO glass substrate is cleaned, dried and pretreated.
The BODIPY derivative (BODIPY-X or Pt-BODIPY-X) disclosed by the invention is a novel BODIPY derivative, when the BODIPY derivative forms a P/N heterojunction, a larger built-in electric field can be formed in a depletion layer at an interface, and the direction of the electric field is opposite to that of an external electric field, so that the dissociation of excitons is facilitated; the HOMO energy level difference between the BODIPY derivative and the hole transport layer is similar, and the BODIPY derivative and the N-type semiconductor material PC61BM have relatively matched energy level difference to provide proper dissociation energy E for exciton dissociationDAThe energy level structure is more optimized, and the photocurrent, the light responsivity and the light detectivity of the device can be effectively improved; in addition, the boron dipyrromethene derivative disclosed by the invention does not need to be added with Pd (PPh3)4 palladium catalyst in the preparation process, so that the overall manufacturing cost of the device is reduced, and the generation of hazardous wastes is reduced.
In addition, it is further preferable that the donor material BODIPY derivative adopted by the photoelectric detector is preferably a Pt-BODIPYL BODIPY derivative (Pt-BODIPY-X), and the heavy atom effect of the Pt can be used to red shift the absorption band of the BODIPY derivative material by 50nm, thereby further widening the detection range of the photoelectric detector; the platynyl BODIPY derivative (Pt-BODIPY-X) has higher light absorption coefficient in near infrared, and has wider absorption spectrum compared with photosensitive dyes such as phthalocyanine, porphyrin, squalene and the like in the prior art.
The device structure and the manufacturing process of the optical detector disclosed by the invention are simple, are insensitive to temperature, have low cost, high responsivity, high response speed of the detector, small volume and high stability, can be prepared on a flexible substrate, and have good application value in the fields of photoelectric communication and the like.
Drawings
Fig. 1 is a schematic structural composition diagram of a photodetector according to embodiment 2 of the present invention;
FIG. 2 is a nuclear magnetic hydrogen spectrum of Pt-BODIPY-DN from the Pt-alkynyl-BODIPY dipyrrole derivative according to example 1 of the present invention;
FIG. 3 is a UV-VIS absorption spectrum of BODIPY-DN and Pt-BODIPY-DN of BODIPY derivative materials of test example 1 of the present invention;
fig. 4 is a schematic view of a current-voltage curve of the photodetector device 1 according to test example 2 of the present invention in a dark state and a bright state;
FIG. 5 is a graph showing the relationship between the responsivity and the specific detectivity of the organic photodetector device 1 at-5V for the photodetector device 1 according to test example 2 of the present invention.
Detailed Description
In order to make the technical solutions of the present invention better understood, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention.
Example 1: process for preparing BODIPY derivatives
The preparation method of the BODIPY derivative comprises the following synthetic route:
Figure BDA0002992231830000051
the preparation method of the BODIPY derivative specifically comprises the following steps: in the compound 1, X is any one of Dimethylamino (DN), anilino (TPN) and triphenyl phosphonium (TPP); adding the compound 1 and acetylbenzyne into a 50mL double-mouth bottle, and protecting with nitrogen; first, 10mL of 10% NaOH solution was added. 15mL of ethanol was added and dissolved completely. Reacting for 8 hours to obtain a compound 2; 0.27g of Compound 2 was combined with 5mL of diethylamine, 5mL of CH3NO2The mixture was sequentially charged into a 50mL single-necked flask and dissolved in 10mL of methanol. Reacting at 80 ℃ for 12h to obtain the compound 3. 0.40g of Compound 3 and 5g of ammonium acetate were dissolved in 20mL of n-butanol and reacted at 70 ℃ for 12 hours to give Compound 4. And (5) protecting with nitrogen. 0.400g of Compound 4 and 5mL of DIPEA were dissolved in 20mL of redistilled dichloromethane, reacted at room temperature for 30min, and then 5mL of boron trifluoride diethyl ether was slowly dropped. Reacting for 3h at normal temperature to obtain a compound 5 (namely BODIPY-X) under the protection of nitrogen. Compound 5, Pt (PBu)3)2Cl2And CuI is placed in a single-neck flask and protected by nitrogen. Then 10mL of DCM was re-evaporated. Then adding 7mL of redistilled triethylamine, and reacting for 12h to obtain Pt-BODIPY-X.
The nuclear magnetic hydrogen spectrum of the synthesized Pt-BODIPY-DN is shown in FIG. 2.
Test example 1: UV-VISIBLE ABSORPTION TESTING OF FLUOROBOBONYROLE DERIVATIVES
BODIPY-DN and Pt-BODIPY-DN were specifically tested from BODIPY-X and Pt-BODIPY-X prepared in example 1; in the invention, X in the BODIPY-X and Pt-BODIPY-X represents three substituents, the chemical properties of the BODIPY-X substituted by the three substituents are the same, and the chemical properties of the Pt-BODIPY-X are also the same, so that the test is only carried out by the BODIPY-DN and the Pt-BODIPY-DN in the embodiment.
The testing process comprises the following steps: an UV-2501PC ultraviolet-visible spectrophotometer is used for carrying out ultraviolet-visible absorption tests on BODIPY derivative films (BODIPY-DN and Pt-BODIPY-DN) which are coated on a quartz glass substrate in a spinning way, as shown in figure 3, the test results show that the absorption peak positions of BODIPY materials are all positioned in the range of near infrared wavelength 600-1000nm, and the higher absorption coefficient shows that the BODIPY materials have better application effect in a photoelectric detector.
Example 2: photodetector structure and method of manufacture
This example specifically describes the structure and preparation method of an active layer of a heteroj unction type broad spectrum detector of a BODIPY derivative, taking one specific device as an example.
The structural schematic diagram of the heterojunction-type broad spectrum detector of the BODIPY derivative is shown in figure 1. As can be seen from the figure, the heterojunction-type broad spectrum detector of the BODIPY derivative sequentially comprises from bottom to top: transparent conductive substrate 1, hole transport layer 2, active layer 3, electron transport layer 4, electron buffer layer 5 and metal cathode 6. The heterojunction is adjacent to the hole transport layer and the electron transport layer; the device structure of the embodiment can be simply expressed as: device 1: ITO/PEDOT: PSS/Pt-BODIPY-DN/PC61BM/C60LiF/Al, ITO glass substrate in which the transparent conductive substrate is an anode, PEDOT: PSS as hole transport layer, Pt-BODIPY-DN and PC61Mixtures of BM as active layer, C60The anode material is used as a hole blocking layer, LiF is used as an electron buffer layer, and metal Al is used as a cathode.
The specific manufacturing steps of the device of the embodiment are as follows:
step 1: carrying out ultrasonic treatment on the ITO glass substrate for 15 minutes respectively by acetone, isopropanol and deionized water, and then putting the ITO glass substrate into an infrared drying oven for drying;
step 2: placing the cleaned ITO glass substrate in an ultraviolet ozone instrument for surface hydrophilic treatment for 15 minutes;
and step 3: and (3) spin-coating PEDOT on the ITO glass substrate after surface hydrophilic treatment: PSS, the spin-coating speed is 3000rpm, the spin-coating time is 30s, and then annealing treatment is carried out on a hot bench at 120 ℃ for 20 minutes;
and 4, step 4: in the PEDOT: the PSS film is coated with a spin-coating active layer at the speed of 1000rpm for 30s, and then annealed at 120 ℃ for 10 minutes on a hot bench; the thickness is 100 nm;
and 5: 5X 10 on the active layer film by vacuum deposition-5Vapor deposition of C under pressure of Pa60The deposition speed is 1nm/s, the thickness is 10nm,
step 6: at C60Vacuum deposition on film at 5X 10-5Evaporating an electronic buffer layer LiF under the pressure of Pa, wherein the deposition speed is 0.1nm/s, and the thickness is 1 nm;
and 7: vacuum evaporation method is used for 5X 10 on the electron transport layer LiF film-5And evaporating metal cathode Al under the pressure of Pa, wherein the deposition speed is 3nm/s, and the thickness is 100 nm.
Test example 2: photodetector structure spectral response test
The broad-spectrum detector prepared in example 2 is used for testing, and the prepared optical detection device is placed on an optical spectral response testing system (IPCE) of QEM24-S to test the photocurrent, the optical responsivity and the optical detection rate of the detector under the full-light excitation light.
In the process of testing the electric detector, exciting light is emitted into the photoelectric detector from one side of the transparent conductive substrate. Fig. 4 shows bright and dark currents of the BODIPY derivative heterojunction type detector in a dark state and under illumination. It can be seen from the figure that the device exhibits a large photocurrent at a fixed wavelength of illumination. The photocurrent and dark current of the device at-5V are respectively: 0.38mA and 2.3X 10-2And mA. As shown in fig. 5, it is calculated that the optical responsivity of the device is 130mW, and the optical detectivity of the device is: 2.4X 1011Jones。EDAThe energy level difference between the HOMO energy level of the BODIPY derivative and the hole transport layer is 0.23eq, the energy level structure is optimized, and the photocurrent, the photoresponse and the optical detectivity of the device can be effectively improved.
Although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments described in the foregoing detailed description, or equivalent changes may be made in some of the features of the embodiments described above. All equivalent structures made by using the contents of the specification and the attached drawings of the invention can be directly or indirectly applied to other related technical fields, and are also within the protection scope of the patent of the invention.

Claims (8)

1. The application of the BODIPY derivative as a donor material of an active layer of a photoelectric detector is characterized in that the molecular structural formula of the BODIPY derivative is any one of the following:
Figure FDA0003574301560000011
wherein n is more than or equal to 1.
2. A boron-dipyrromethene derivative is used as a donor-doped photoelectric detector, and is characterized in that: the ITO conductive glass layer, the hole transport layer, the active layer, the hole barrier layer, the electron buffer layer and the metal cathode layer; the hole transport layer is PEDOT: PSS; the active layer is composed of a heterojunction film formed by mixing a heterojunction donor material and a heterojunction acceptor material, wherein the heterojunction donor material is the BODIPY derivative of claim 1, and the heterojunction acceptor material is fullerene or a fullerene derivative; the fullerene derivative is C60、C70、PC61BM、PC71Any one of BMs; the hole blocking layer is composed of an electron transport material having a lower HOMO potential; the electronic buffer layer is composed of LiF; the metal cathode layer is composed of a metal having a low work function.
3. The BODIPY derivative as donor-doped photodetector of claim 2, wherein the thickness of the heterojunction film is 60-150 nm.
4. The BODIPY derivative as donor-doped photodetector of claim 2, wherein the heterojunction film is prepared by spin coating.
5. The class of BODIPY derivatives as donor-doped photodetectors of claim 2, wherein the hole transport layer has a PEDOT: the PSS film is formed on an ITO glass substrate by spin coating by a solution method, and the thickness of the film is 20-40 nm.
6. The BODIPY-based doped photodetector of claim 2, wherein the hole blocking layer is a fullerene material C60TPBi and Balq, the film thickness is 8-12 nm.
7. The BODIPY derivative as donor-doped photodetector of claim 2, wherein the thickness of the electron buffer layer is 1-3 nm.
8. The BODIPY derivative as donor-doped photodetector of claim 2, wherein the metal cathode layer is Ag or Al thin film with a thickness of 80-120 nm.
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