Double boron embedded polycyclic aromatic hydrocarbon functional molecular materials and their preparation and application

Abstract

This invention belongs to the field of optoelectronic materials and specifically discloses a diboron-embedded polycyclic aromatic hydrocarbon functional molecular material. The invention also discloses methods for preparing and applying the diboron-embedded polycyclic aromatic hydrocarbon functional molecular material. The invention fuses pyrene and benzothiophene in three dimensions to construct a diboron-embedded polycyclic aromatic hydrocarbon functional molecule via a hybrid fusion method. By regulating the type of dopant atoms, the π-electron conjugated structure of the conjugated molecule, and its physical properties, the resulting material becomes a functional organic molecular material with charge transport properties and visible / near-infrared luminescence. This functional material can be used in electronic devices.

Description

Technical Field

[0001] The present invention relates to the field of functional molecular materials, in particular to molecular materials with photoelectric properties. Background Art

[0002] Polycyclic aromatic hydrocarbons (PAHs) molecules are widely used in organic field-effect transistors, organic light-emitting diodes, and organic photovoltaics because their structures can be controlled and designed and they often exhibit predictable optoelectronic properties. Rearranging the topological structure of the six-membered ring or incorporating heteroatoms is an effective strategy to change the optoelectronic properties of molecules. In recent years, chemists have focused a lot of attention on introducing heteroatoms to precisely regulate the optoelectronic properties of PAHs. Replacing some carbon atoms in polycyclic aromatic hydrocarbons with heteroatoms to form a doped conjugated carbon skeleton can significantly improve the stability and assembly performance of the molecules, thereby improving the optoelectronic properties of organic optoelectronic materials. Among them, boron atoms are mainly due to the presence of p z The empty orbitals allow it to act as both an electron acceptor and a Lewis acid. When incorporated into polycyclic aromatic hydrocarbons (PAHs), the molecular orbital energy and band gap can be significantly reduced, particularly at the LUMO energy level. Therefore, boron-doped PAHs are often considered excellent visible-light emitting materials and n-type materials. This has a significant impact on the development of organic optoelectronic devices, as the emission bands of currently studied luminescent materials are mostly concentrated in the ultraviolet, and the research and application of organic semiconductor materials are mostly focused on p-type materials. However, boron atoms are very sensitive to oxygen and water in the air, which greatly limits the development of boron-doped PAHs. Summary of the Invention

[0003] In response to the existing problems, the first purpose of the present invention is to provide a double boron embedded polycyclic aromatic hydrocarbon functional molecular material, aiming to provide a new structural compound with excellent transmission efficiency and good application value in optoelectronic materials.

[0004] The second purpose of the present invention is to provide a method for preparing the double boron embedded polycyclic aromatic hydrocarbon functional molecular material, aiming to successfully prepare the double boron embedded polycyclic aromatic hydrocarbon functional molecular material.

[0005] The third object of the present invention is to provide the use of the double boron embedded polycyclic aromatic hydrocarbon functional molecular material in the preparation of optoelectronic materials such as organic field effect transistors.

[0006] The fourth object of the present invention is to provide a functional molecular material containing the double boron embedded polycyclic aromatic hydrocarbons, which can be used as a sensor for detecting fluorides harmful to the environment.

[0007] A double boron embedded polycyclic aromatic hydrocarbon functional molecular material having a structural formula 1:

[0008]

[0009] In formula 1, X1 is O, S or NR;

[0010] R1 is H, alkyl, substituted alkyl, cycloalkyl, aryl or substituted aryl;

[0011] R2 is an alkyl group, a substituted alkyl group, a cycloalkyl group, an aryl group or a substituted aryl group;

[0012] The substituents in the substituted alkyl and substituted aryl groups are at least one of halogen, CN, C1-C6 alkyl, C1-C6 alkoxy, and trifluoromethyl.

[0013] The present invention provides a compound with a completely new three-dimensional conjugated structure, and the compound has integrated charge migration properties and excellent transmission efficiency.

[0014] In the present invention, the control of the molecular structure and groups is the key to synergistically improving the transmission efficiency and the application performance of the optoelectronic material.

[0015] In the present invention, the alkyl group is C1-C 24 preferably a C1-C6 straight or branched chain alkyl group.

[0016] The substituted alkyl group is C1-C 24 Preferably, it is a substituted alkyl group having one or more substituents on the C1-C6 carbon chain;

[0017] The aryl group is a phenyl group, a five-membered heterocyclic aryl group, a six-membered heterocyclic aryl group, a condensed ring or a condensed heterocyclic group formed by combining any two or more aromatic rings of a benzene ring, a five-membered heterocyclic aryl group, or a six-membered heterocyclic aryl group;

[0018] Preferably, the aryl group is a phenyl group;

[0019] Preferably, the substituted aryl group is a substituted aryl group having one or more substituents on the aromatic ring; preferably a substituted phenyl group;

[0020] Preferably, the substituent in the substituted alkyl group or the substituted aryl group is at least one of a C1-C6 alkyl group, a C1-C6 alkoxy group or a halogen.

[0021] Preferably, the double boron embedded polycyclic aromatic hydrocarbon functional molecular material, wherein the X1 is O or S;

[0022] The R1 is H;

[0023] The R2 is a phenyl group or a substituted phenyl group; the substituted phenyl group is a phenyl group substituted with at least one substituent selected from the group consisting of a C1-C6 alkyl group, a C1-C6 alkoxy group, a halogen group, and a CN group.

[0024] The biboron-embedded polycyclic aromatic hydrocarbon functional molecular material of the present invention has a rigid π-conjugated skeleton, strong intermolecular interactions, and a low LUMO energy level. In addition, it has the typical characteristics of an n-type semiconductor, and its electron transfer efficiency in the film is 1.49×10 -3 cm 2 V -1 s -1 .

[0025] The present invention also provides a method for preparing the double boron embedded polycyclic aromatic hydrocarbon functional molecular material, which is prepared by a ring-closing reaction of a compound of formula 2, an alkyl lithium, a boron source and R2MgX (Grignard reagent);

[0026]

[0027] In Formula 2, the selection ranges of X1 and R1 are the same as those in Formula 1;

[0028] The X is a halogen;

[0029] The selection range of R2 in the R2MgX is the same as that of Formula 1.

[0030] The present invention has found that by adopting Formula 2 to carry out a ring-closing reaction in a combined system of alkyl lithium and Grignard reagent, the required double boron embedded polycyclic aromatic hydrocarbon functional molecular material can be prepared in one step, and it helps to improve the yield and purity of the preparation.

[0031] In the present invention, the alkyl lithium is a C1-C6 linear or branched alkyl lithium, preferably butyl lithium;

[0032] Preferably, the boron source is at least one of BBr3, BCl3, and BF3;

[0033] Preferably, in Formula 2, X is preferably Br.

[0034] Preferably, in the R2MgX, X is Cl, Br or I.

[0035] Preferably, the molar ratio of the compound of formula 2, alkyl lithium, boron source and R2MgX is 1:2-2.5:2-2.5:4-7; more preferably 1:2.1-2.3:2.1-2.3:5.5-6.5.

[0036] Preferably, the compound of formula 2, alkyl lithium, and boron source are mixed in the first stage before the first stage reaction, and then mixed with R2MgX in the second stage before the second stage reaction;

[0037] The temperature of the first mixing stage and the second mixing stage is less than or equal to 4°C, for example, -4 to 4°C;

[0038] The temperature of the first stage reaction is 100-140°C, preferably 105-125°C;

[0039] The temperature of the second stage reaction is 15-40°C, preferably 20-35°C;

[0040] The reaction time of each stage can be determined based on TLC control. For example, the first stage reaction time is 2 to 8 hours; the second stage reaction time is 0.5 to 2 hours.

[0041] Preferably, the solvent in the reaction stage is at least one of chlorobenzene, toluene, and o-xylene;

[0042] Preferably, the ring-closure reaction is carried out under anhydrous and oxygen-free conditions.

[0043] In the present invention, the formula 2 can be prepared based on a known halogenation reaction. For example, in the present invention, the

[0044] Formula 2 is prepared by halogenation reaction of a compound of formula 3 with a halogenating agent:

[0045]

[0046] In the formula 3, the selection ranges of X1 and R1 are the same as those in formula 1;

[0047] Preferably, the halogenating agent is liquid bromine. In the present invention, the use of liquid bromine is conducive to the efficient and successful preparation of the target product.

[0048] Preferably, the solvent for the halogenation reaction is at least one of DCM, carbon tetrachloride, DMF and chloroform;

[0049] Preferably, the molar ratio of the compound of formula 3 to the halogenating agent is 1:2 to 8; preferably 1:2 to 2.2;

[0050] Preferably, the temperature of the halogenation reaction is 15-35°C.

[0051] In the present invention, the formula 3 can be prepared based on a conventional coupling reaction such as Suzuki coupling. For example, the formula 3 is prepared by Suzuki coupling reaction of formula 4 and formula 5:

[0052]

[0053] The selection ranges of X1 and R1 in formula 4 are the same as those in formula 1;

[0054] A in Formula 5 is X (halogen) or OTF;

[0055] Preferably, the molar ratio of Formula 4 to Formula 5 is 2 to 3:1, preferably 2.2 to 2.5:1;

[0056] Preferably, the Suzuki coupling reaction is carried out under the catalysis of palladium, and the preferred catalyst is Pd(PPh3)4; the amount of the catalyst used is a catalytic amount, for example, 0.1 to 1% of the molar amount of formula 5.

[0057] Preferably, the temperature of the Suzuki coupling reaction is 80-95°C, more preferably 85-90°C.

[0058] The reaction time can be determined by TLC.

[0059] The present invention provides an application of the double boron embedded polycyclic aromatic hydrocarbon functional molecular material, and the conjugated functional molecule is used in the fields of organic optoelectronic materials, multifunctional devices and functional materials.

[0060] More preferably, the three-dimensional conjugated molecular material is used to prepare organic field effect transistors, organic light emitting diodes, polarized light emitting organic field effect transistors, etc.

[0061] The present invention also provides an electronic device comprising the double boron embedded polycyclic aromatic hydrocarbon functional molecular material;

[0062] Preferably, the electronic device is at least one of an organic field effect transistor, an organic light emitting diode, and a polarized light emitting organic field effect transistor.

[0063] Beneficial effects

[0064] The present invention provides a novel compound of Formula 1. Research has also found that the compounds of Formula 1, based on their structural combination, can achieve overall synergy, exhibit visible / near-infrared fluorescence properties, and can be used as detectors for detecting environmentally harmful fluorides; exhibit integrated charge transfer properties, and exhibit excellent transmission efficiency.

[0065] The present invention innovatively provides the described double-boron-embedded polycyclic aromatic hydrocarbon functional molecule, achieving the construction of an environmentally stable polycyclic aromatic hydrocarbon (B2X2) embedded with two X1 and two boron atoms. This makes it a functional integrated material with charge transport properties, which can be applied to electronic devices and optical components targeting high-end material requirements. BRIEF DESCRIPTION OF THE DRAWINGS

[0066] Figure 1 This is the H-NMR chart of the prepared compound of formula 2-A.

[0067] Figure 2 is the C-NMR chart of the prepared compound of formula 2-A.

[0068] Figure 3 This is the H-NMR chart of the prepared compound of formula 1-A.

[0069] Figure 4is the C-NMR chart of the prepared compound of formula 1-A.

[0070] Figure 5 is the B-NMR chart of the prepared compound of formula 1-A.

[0071] Figure 6 is the mass spectrum of the prepared compound of formula 2-A.

[0072] Figure 7 is the mass spectrum of the prepared compound of formula 1-A.

[0073] Figure 8 It is the single crystal diffraction structure diagram of the prepared compound of formula 1-A.

[0074] Figure 9 1-A is the absorption spectrum and emission spectrum of the prepared compound of formula 1-A.

[0075] Figure 10 The UV-visible spectrum of the prepared compound of formula 1-A was obtained by fluoride ion complexometric titration.

[0076] Figure 11 It is the theoretical calculation diagram of the simulated absorption spectrum of the prepared compound of formula 1-A.

[0077] Figure 12 1-A is a theoretical calculation diagram of the molecular orbital distribution of the prepared compound of formula 1-A.

[0078] Figure 13 Graph showing the transfer characteristics of a top-gate, bottom-contact OFET based on a thin film of the compound of formula 1-A.

[0079] Figure 14 Graph showing the output characteristics of a top-gate, bottom-contact OFET based on a thin film of the compound of formula 1-A. DETAILED DESCRIPTION

[0080] test:

[0081] NMR determination: Compounds 1-A and 2-A were measured on a BRUKER 400 MHz nuclear magnetic resonance spectrometer to obtain NMR spectra.

[0082] Mass spectrometry: Compounds 1-A and 2-A were analyzed and analyzed on a Finnigan MAT TSQ 7000 mass spectrometer.

[0083] Electrochemical testing: Tetrabutylammonium hexafluorophosphate (0.1 mol / L) was added to a 1 mmol / L anhydrous tetrahydrofuran solution of compound 1-A. Cyclic voltammetry (CV) curves were performed using a Shanghai Chenhua 650D electrochemical workstation under nitrogen protection, with a glassy carbon electrode as the working electrode, an Ag / AgCl electrode as the reference electrode, and a Pt wire electrode as the counter electrode. The scan rate was 50 mVs. -1 Finally, use Fc / Fc + (Fc is ferrocene) for calibration.

[0084] Spectral test: Prepare dichloromethane solutions of compound formula 1-A and 2-A respectively, with a concentration of 10 -5 mol / L, and the steady-state UV-Vis absorption spectra were tested and recorded on a Shimadzu UV-3600PLUS.

[0085] Single Crystal X-ray Analysis: n-hexane was added to a chloroform solution of the product of Formula 1-A, followed by slow evaporation at -20°C to obtain single crystals suitable for X-ray crystallography. Data were collected on an Agilent Supernova X-ray diffractometer.

[0086] Theoretical calculations: Gauss 09 software was used to analyze the electronic transitions of compound 1-A using density functional theory (DFT) and time-resolved density functional theory (TD-DFT) theoretical calculations.

[0087] Example 1

[0088] Synthesis of Formula 2-A:

[0089] Chemical synthesis method is shown in design formula 1:

[0090]

[0091] Weigh 1.0 g (2.36 mmol) of Formula 5-A and 1.1 g (5.9 mmol) of Formula 4-A into a two-necked flask, add 40 mL of dioxane, stir thoroughly, and dissolve. Add 5 mL (10 mmol) of a 2 mol / L aqueous solution of KCO, purge, and purge the mixture with argon for 30 minutes. Under argon, add 423 mg (0.02 mmol) of Pd(PPh) to the mixture. The reaction mixture is heated and stirred at 90°C for 2 hours, then cooled to room temperature and the solvent is removed by rotary evaporation. The residue is extracted with a mixture of water and dichloromethane (1:3 by volume). The organic phase is collected and dried over anhydrous NaSO. The solvent is removed by rotary evaporation and the mixture is eluted directly from ethyl acetate to obtain the intermediate product of Formula 1 (Formula 3-A) (823 mg, 2.1 mmol, 89% yield).

[0092] The above product was dissolved in dichloromethane, and 230 μL (4.4 mmol) of liquid bromine was then added dropwise to the solution. The mixture was stirred at room temperature for 30 minutes and then quenched with a 2 mol / L aqueous Na2S2O4 solution (10 mmol). The residue was extracted with a mixed solution of water and dichloromethane (volume ratio of 1:3). The organic phase was collected and dried over anhydrous Na2SO4. The solvent was removed by rotary evaporation and the mixture was directly eluted from ethyl acetate to obtain Formula 2-A (1.6 g, yield 97%).

[0093] The structure of the compound of formula 2-A was confirmed by hydrogen nuclear magnetic resonance spectroscopy, carbon nuclear magnetic resonance spectroscopy, mass spectrometry, ultraviolet visible spectroscopy, single crystal diffraction and the like.

[0094] 1 H NMR(400MHz, CDCl3)δ7.95(d,J=7.9Hz,2H),7.91(d,J=7.9Hz,4H),

[0095] 7.70(s,2H),7.56(t,J=7.5Hz,4H),7.49(t,J=7.3Hz,4H).

[0096] 13 C NMR (100MHz, CDCl3) δ138.76,138.30,136.45,132.17,132.00,130.52,128.54,126.95,126.56,125.70,125.38,123.61,122.28,108.87.

[0097] HRMS m / z:Calcd for C 26 H 14 Br2S2[M] + 549.8900; Found 549.8321(error=-1.1

[0098] ppm).

[0099] Synthesis of Formula 1-A

[0100] Chemical synthesis method is shown in Design Formula 2:

[0101]

[0102] At 0°C, 1.1 mL of n-butyllithium in n-hexane (2.2 mol / L, 2.3 mmol) was added dropwise to a 30 mL toluene solution of the compound of Formula 2-A (1.09 mmol). The mixture was stirred at 0°C for 0.5 h, followed by the addition of 2.4 mL of BBr in n-hexane (1.0 mol / L, 2.4 mmol), and the mixture was stirred at 0°C for 1 h. The temperature was then raised to 110°C and stirred for 6 h. After the reaction was complete, 6.6 mL of mesityl magnesium bromide in tetrahydrofuran (1.0 mol / L, 6.6 mmol) was added dropwise to the reaction mixture at 0°C. The mixture was then slowly heated to room temperature (25-30°C) and stirred for 1 h. The solvent was removed by rotary evaporation under reduced pressure, and the crude product was purified by column chromatography (petroleum ether / CH2Cl2 = 10:1) and recrystallized from dichloromethane to obtain Formula 1-A (289 mg, 41% yield).

[0103] The product 1-A was tested for its performance using a top-gate bottom-contact OFET device structure. The substrate used in the experiment was a glass substrate. First, the substrate was ultrasonically cleaned with deionized water, acetone, and isopropanol for 1 minute each. After cleaning, the residual isopropanol solution on the surface was quickly blown away with an argon gun. Next, the substrate surface was treated with ultraviolet ozone for 15 minutes to further clean the substrate surface. Then, a 40nm gold electrode was evaporated using an evaporator with a vacuum degree of 3×10 -4 pa, the evaporation rate is 5A / S, and the shape of the source and drain electrodes is controlled by a mask process; then a chlorobenzene solution of formula 1-A with a concentration of 5mg / mL is prepared and a thin film is prepared by spin coating (1500rpm, 20s); the vacuum degree and evaporation rate of the vacuum evaporator are kept constant, and a CYTOP insulating layer is evaporated by the evaporator, and the solute to solvent ratio of CYTOP is 3:1; finally, an aluminum gate electrode is evaporated with a thickness of 100nm. According to the relationship between the drain current and the square root of the gate voltage relative to the gate voltage, the charge carrier mobility of the OFET is calculated to be 1.49×10 -3 cm 2 V -1 s -1 .

[0104]

[0105] The structure of the compound of formula 1-A was confirmed by hydrogen nuclear magnetic resonance spectroscopy, carbon nuclear magnetic resonance spectroscopy, mass spectrometry, ultraviolet visible spectroscopy, single crystal diffraction and the like.

[0106] The emission spectrum of Formula 1-A shows that the compound Formula 1-A has a fluorescence band in the visible light / near-infrared region, with a maximum fluorescence wavelength of 680 nm and a fluorescence quantum yield of 8.0%, which indicates that the excited state of Formula 1-A has certain intramolecular charge transfer characteristics.

[0107] 1 H NMR (400MHz, CDCl3) δ8.24(s,2H),7.98(s,2H),7.87(d,J=7.8Hz,2H),7.30(t ,J=8.9Hz,4H),7.17(t,J=7.4Hz,2H),6.93(s,4H),2.41(s,6H),2.05(s,12H);

[0108] 13 C NMR (100MHz, CDCl3) δ159.63,144.47,142.09,139.76,138.14,137.13,133.38,127.82,127.19,125.62,125.36,124.78,121.94;

[0109] 11 B NMR (128MHz, CDCl3) δ32.42; HRMS m / z:Calcd for C 44 H 35 B2S2[M] + 648.2300; Found 648.2315(error=+0.3ppm).

[0110] Comparative Example 1

[0111] Synthesis of Formula 1-B

[0112]

[0113] Compared with Example 1, the only difference was that the raw material of Formula 5-B in this case replaced Formula 5-A in Example 1. The other operating steps and parameter controls were the same. The crude product was washed with ethyl acetate to obtain 289 mg of pure white product 1-B, with a yield of 41%. Due to the poor solubility of the product 1-B molecule, the spin-coated film quality was very poor, which resulted in poor electron transport properties of the product of Formula 1-A.

[0114] Comparative Example 2

[0115] Synthesis of Formula 2-A

[0116]

[0117] Compared with Example 1, the only difference is that NBS is used instead of liquid Br2 in this example. NBS is added dropwise to the dichloromethane solution of the product formula 3-A at room temperature and under heating conditions, respectively, but the target product formula 2-A is not obtained.

Claims

1. A double boron embedded polycyclic aromatic hydrocarbon functional molecular material, characterized in that: It has the structural formula 1: Formula 1 In formula 1, X1 is O or S; The R1 is H; The R2 is a phenyl group or a substituted phenyl group; the substituted phenyl group is a phenyl group substituted with at least one substituent selected from the group consisting of a C1-C6 alkyl group, a C1-C6 alkoxy group, a halogen group, and a CN group.

2. The double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 1, characterized in that: The X1 is S; The R1 is H; The R2 is mesityl.

3. A method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to any one of claims 1 to 2, characterized in that: Prepared by ring-closing reaction of compound of formula 2, alkyl lithium, boron source and R2MgX; Formula 2 In Formula 2, the selection ranges of X1 and R1 are the same as those in Formula 1; The X is a halogen; The selection range of R2 in the R2MgX is the same as that of Formula 1.

4. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 3, characterized in that: The alkyl lithium is a C1-C6 straight chain or branched chain alkyl lithium.

5. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 4, characterized in that: The alkyl lithium is butyl lithium.

6. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 3, characterized in that: The boron source is at least one of BBr3, BCl3, and BF3.

7. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 3, characterized in that: The molar ratio of the compound of formula 2, alkyl lithium, boron source and R2MgX is 1:2~2.5:2~2.5:4~7.

8. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 3, characterized in that: The compound of formula 2, alkyl lithium, and boron source are mixed in the first stage before the first stage reaction, and then mixed with R2MgX in the second stage before the second stage reaction; The temperature of the first mixing stage and the second mixing stage is less than or equal to 4°C; The temperature of the first stage reaction is 100~140℃; The temperature of the second stage reaction is 15~40 ℃.

9. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 8, characterized in that: The solvent in the reaction stage is at least one of chlorobenzene, toluene, and o-xylene; The ring-closure reaction is carried out under anhydrous and oxygen-free conditions.

10. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to any one of claims 3 to 9, characterized in that: The compound of formula 2 is prepared by halogenation reaction of a compound of formula 3 with a halogenating agent: Formula 3 In Formula 3, the selection ranges of X1 and R1 are the same as those in Formula 1.

11. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 10, characterized in that: The halogenating agent is liquid bromine; The solvent for the halogenation reaction is at least one of DCM, carbon tetrachloride, DMF, and chloroform; The molar ratio of the compound of formula 3 to the halogenating agent is 1:2 to 8; The temperature of the halogenation reaction is 15~35 ℃.

12. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 10, wherein: Formula 3 is prepared by Suzuki coupling reaction of Formula 4 and Formula 5: Formula 4 Formula 5 The selection ranges of X1 and R1 in formula 4 are the same as those in formula 1; A in Formula 5 is X or OTF.

13. The method for preparing a double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to claim 12, characterized in that: The molar ratio of formula 4 to formula 5 is 2-3:1; The Suzuki coupling reaction is carried out under the catalysis of palladium, wherein the catalyst is Pd(dppf)Cl2; The temperature of the Suzuki coupling reaction is 80~95℃.

14. An application of the double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to any one of claims 1 to 2, characterized in that: The invention is used for preparing at least one of organic photoelectric materials, multifunctional devices and functional materials.

15. An electronic device, characterized in that: The invention comprises the double boron embedded polycyclic aromatic hydrocarbon functional molecular material according to any one of claims 1 to 2.

16. The electronic device according to claim 15, wherein The electronic device is at least one of an organic field effect transistor, an organic light emitting diode, and a polarized light emitting organic field effect transistor.

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