Organic electro-optical material capable of being used for waveguide interface functionalization and preparation method and application of organic electro-optical material

Abstract

The invention discloses an organic electro-optical material capable of being used for waveguide interface functionalization and a preparation method and application thereof.A 4-azido-2, 3, 5, 6-tetrafluorobenzene structural unit is introduced into the material, nitrogen-guene generated by the structure under ultraviolet irradiation can be subjected to an insertion reaction with C-H bonds in material molecules or on an interface, and the material can be used as a functional material for waveguide interface functionalization. A solid three-dimensional cross-linked network is formed, meanwhile, a plurality of polar groups and fluorine atoms are provided, interface wettability and physical and chemical bonding force between the material and common waveguide materials such as Si, Si3N4 and SiO2 can be improved, interlayer adhesive force and interface stability in a waveguide structure are remarkably improved, and the performance of the material is improved. And the failure problems of delamination, thermal warping and the like in preparation and long-term operation of the device are reduced.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electro-optical materials, and in particular relates to an organic electro-optical material that can be used for waveguide interface functionalization, and a preparation method and application thereof. Background Art

[0002] Organic electro-optic (EO) materials have become a promising key functional material in the next generation of high-speed optical communication systems and on-chip integrated optoelectronic devices in recent years due to their excellent electro-optical response performance, highly designable molecular structure, and excellent solution processing properties. Compared with traditional inorganic electro-optic crystal materials, such as lithium niobate (LiNbO3) widely used in commercial modulators, organic electro-optic materials have significant advantages, including a higher electro-optic coefficient (r 33 > 200pm / V), a lower dielectric constant, and a smaller drive voltage. These exceptional properties not only effectively shorten the modulator's interaction length, enabling more compact device packaging, but also significantly improve the response rate of optical modulation while reducing power consumption, making them highly attractive for photonic chip applications with extremely demanding performance. In particular, organic electro-optical materials have become a core material system for realizing the next generation of ultra-high-speed, low-power integrated optical modulators on heterogeneous integrated modulation platforms such as silicon-organic hybrid (SOH) and plasmonic-organic hybrid (POH).

[0003] However, despite the excellent physical properties and application potential of existing organic electro-optical materials, their practical application in on-chip integrated optoelectronic devices still faces several key technical challenges, of which the two most prominent issues need to be addressed urgently:

[0004] First, in heterogeneous integrated structures, the interface compatibility between waveguides and electro-optical materials is poor, severely limiting the long-term stability and reliability of the devices. Currently, mainstream integrated photonic devices typically use silicon nitride (Si3N4), silicon oxide (SiO2), or their composite structures as inorganic waveguide materials. These materials differ significantly from organic electro-optical materials in terms of thermal expansion coefficient, interfacial surface energy, and intermolecular interaction forces. This mismatch can easily lead to stress concentration, interface microcracks, peeling, or interlayer debonding during device manufacturing. Furthermore, thermal stress cycles or environmental disturbances can further exacerbate the risk of failure during long-term device operation, ultimately leading to a severe degradation of modulator performance and a shortened lifespan. Therefore, effectively regulating the interface compatibility between organic and inorganic waveguide materials to construct a stable and robust heterostructure interface has become one of the core issues in improving device stability.

[0005] Second, achieving a balance between the ordered arrangement of organic electro-optic molecules after polarization and thermal stability has always been a key challenge in material design. It is well known that the nonlinear optical response of organic electro-optic materials primarily stems from the noncentrosymmetric polarized structure formed by chromophores with large dipole moments in the molecules under the action of an applied electric field. However, this polarized state is typically thermodynamically metastable and susceptible to randomization of molecular orientation due to thermal excitation, aging, or electric field perturbations, resulting in gradual degradation of the material's electro-optical performance over time. To overcome this problem, current research focuses on enhancing the stability of the aligned structure by physically confining polymer matrix segments or by introducing thermal cross-linking reactions. However, these approaches still have significant drawbacks. First, traditional thermal cross-linking typically requires high temperatures, which can conflict with the thermal conditions of the electro-optical poling step, leading to leakage of the polarized electric field or thermal decomposition of sensitive chromophores, resulting in device performance degradation or even failure. Second, if cross-linking reactions are carried out simultaneously during the poling process, the reactive activity can restrict the freedom of molecular motion, reducing the orientation efficiency of the dipole molecules and significantly compromising the material's electro-optical response.

[0006] In response to the above problems, in recent years, some studies have proposed thermal cross-linking strategies based on click chemical reactions (such as azide-alkyne cycloaddition reaction) in order to achieve the construction of cross-linked networks under relatively mild conditions, thereby improving the thermal stability and structural integrity of the material to a certain extent. However, such cross-linking systems often have problems such as slow reaction rate and limited cross-linking density, and while improving stability, they are often accompanied by a significant decrease in the electro-optical performance of the material (r 33 However, the electro-optical response intensity is usually lower than 150 pm / V, which fails to achieve effective coordination and performance balance among interface adaptability, electro-optical response intensity and molecular orientation stability.

[0007] Therefore, there is an urgent need to develop a new material construction and interface control strategy that can achieve precise regulation of the chemical structure of the waveguide interface at the molecular level. This will not only improve the interfacial adhesion and chemical compatibility between organic electro-optical materials and inorganic waveguides, but also effectively promote the high orientation arrangement of dipole molecules during the polarization process, and achieve long-term stability through structural locking after polarization, ensuring that the device can maintain high performance output even in harsh environments. Of particular note is that if the self-assembled monolayer (SAM) technology can be combined to precisely control the surface energy, chemical activity, and adhesion ability of the waveguide interface through chemical modification, and then combined with electric field-induced polarization and light-induced cross-linking strategies, a molecular-level three-dimensional cross-linked network can be quickly constructed after polarization is completed, achieving in-situ "freezing" and long-term locking of the molecular orientation. This will hopefully break the performance bottleneck in existing material design and achieve high r 33, high stability and high compatibility, while promoting the scale, practicality and on-chip integration of high-performance organic electro-optical modulators, laying a solid material foundation for the next generation of high-speed and low-power optical communication chips. Summary of the Invention

[0008] In response to the above-mentioned deficiencies in the prior art, the present invention provides an organic electro-optical material that can be used for waveguide interface functionalization and a preparation method thereof. The material has good electro-optical properties and thermal stability, and strong interface compatibility. Due to the introduction of 4-azido-2,3,5,6-tetrafluorobenzene structural units at both ends of the molecule, the molecule can bond with the pre-modified interface through a nitrene insertion reaction after electric field polarization, thereby enhancing the bonding strength between the organic electro-optical material and the device. At the same time, the molecule maintains a favorable conformation that is highly perpendicular to the electrode, which can effectively solve the problems existing in the prior art.

[0009] To achieve the above-mentioned purpose, the technical solution adopted by the present invention to solve the technical problem is:

[0010] The present invention discloses an organic electro-optical material that can be used for waveguide interface functionalization, and its structural formula is as follows:

[0011]

[0012] Mode

[0013] Wherein, X is one of O and S atoms;

[0014] R1: C1-C10 alkyl, or one of the following groups:

[0015]

[0016] R2: C1-C10 linear or branched alkyl, or one of the following groups:

[0017]

[0018] R3: C1-C10 linear or branched alkyl, or one of the following groups:

[0019] .

[0020] The method for preparing the organic electro-optical material that can be used for waveguide interface functionalization comprises the following steps: and electron acceptor were dissolved in anhydrous ethanol, heated to 75°C for 1 h, and then the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain;

[0021] Among them, the formula The compound structural formula is as follows:

[0022] .

[0023] Mode

[0024] Furthermore, The preparation method of the compound comprises the following steps:

[0025] (1) Sodium ethoxide solution was added to a mixture of an electron donor and an isophorone derivative, heated to 65°C for reaction, and refluxed overnight. After the reaction was completed, the solvent was removed by rotary evaporation, and the mixture was extracted with ethyl acetate three times and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography to obtain compound 2;

[0026] (2) Compound 2 was dissolved in anhydrous N,N-dimethylformamide, and then tert-butyldimethylsilyl chloride and imidazole were added. The reaction was stirred at room temperature overnight. After completion, the mixture was poured into water and extracted with ethyl acetate. The mixture was washed with concentrated brine and dried over magnesium sulfate. The crude product was purified by column chromatography to obtain an orange-red compound 3.

[0027] (3) Add diethyl cyanomethylphosphate dropwise to a tetrahydrofuran solution of sodium hydride under ice bath, continue stirring after the addition is complete, and obtain a clear solution; add an anhydrous tetrahydrofuran solution of compound 3 to the clear solution, and reflux overnight under a protective atmosphere. After the reaction is complete, quench with water, extract with ethyl acetate, dry with magnesium sulfate, and purify by silica gel chromatography, eluting with a mixed solvent of ethyl acetate and hexane to obtain an orange-yellow compound 4;

[0028] (4) At -78°C under a protective atmosphere, a hexane solution of diisobutylaluminum hydride was slowly added to a toluene solution of compound 4. After reacting at -78°C for 2 h, water-wet silica gel was added, and the mixture was returned to room temperature and stirred for 2 h. After the hydrolysis was completed, the filtrate was filtered, the solvent was evaporated, and the filtrate was purified by silica gel chromatography, eluting with a mixed solvent of ethyl acetate and hexane to obtain an orange-red compound 5.

[0029] (5) Tetrabutylammonium fluoride solution was added dropwise to the tetrahydrofuran solution of compound 5, reacted at room temperature for 0.5 h, poured into water, extracted with ethyl acetate three times, dried over magnesium sulfate, and the solvent was dried to obtain orange-red compound 6;

[0030] (6) 4-azido-2,3,5,6-tetrafluorobenzoic acid, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and 4-dimethylaminopyridine were dissolved in anhydrous dichloromethane to react and obtain a clear solution; a dichloromethane solution of compound 6 was added to the solution, and the temperature was raised to room temperature and reacted overnight. After the reaction was completed, the solution was poured into water, extracted with ethyl acetate three times, and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography to obtain an orange-red compound 7, which is the formula compound.

[0031] Furthermore, the electron acceptor structure is as follows As shown:

[0032] .

[0033] Mode

[0034] Furthermore, the electron donor structure in step (1) is as follows: As shown:

[0035]

[0036] Mode .

[0037] The application of the above-mentioned organic electro-optical material that can be used for waveguide interface functionalization in the preparation of optoelectronic device thin film materials.

[0038] The beneficial effects produced by the present invention are:

[0039] 1. The material of the present invention can enhance the adaptability of the waveguide interface: the material introduces a 4-azido-2,3,5,6-tetrafluorobenzene structural unit. The nitrene generated by this structure under ultraviolet light irradiation can undergo insertion reaction with the C–H bonds inside the material molecules or on the interface to form a strong three-dimensional cross-linked network. At the same time, it provides multiple polar groups and fluorine atoms, which helps to improve the interface wettability and physical and chemical bonding between the material and common waveguide materials such as Si, Si3N4, and SiO2, significantly improve the interlayer adhesion and interface stability in the waveguide structure, and reduce failure problems such as delamination and thermal warping during device preparation and long-term operation.

[0040] 2. The material of the present invention can improve thermal stability: the photocrosslinking reaction can be completed at low temperature, effectively increasing the glass transition temperature (T g ), fixes the orientation structure of the chromophore molecules and significantly suppresses thermally induced relaxation behavior, thereby ensuring the stability of the device's electro-optical performance under high temperature or long-term operation.

[0041] 3. The material of the present invention can maintain a high electro-optic coefficient: Different from traditional thermal cross-linking, optical cross-linking is triggered at low temperature after polarization orientation, avoiding the interference of high temperature treatment on the orientation structure and the weakening of the polarization field, so that the material can still maintain high electro-optical response performance (r 33 > 200 pm / V), achieving a balance between performance and stability.

[0042] 4. The materials of the present invention are compatible with microelectronics manufacturing processes: the UV-induced cross-linking process does not require high-temperature treatment, significantly reducing the process thermal budget. It can be highly compatible with mainstream semiconductor processes (such as photolithography, etching, and packaging), and is particularly suitable for devices such as integrated waveguide modulators on silicon-based optoelectronic platforms.

[0043] 5. The material cross-linking process in the present invention is highly controllable: the photocross-linking process can precisely adjust the degree of cross-linking by adjusting parameters such as light intensity, exposure time, and mask pattern, thereby avoiding the inconsistent cross-linking phenomenon caused by uneven temperature distribution in thermal cross-linking, and effectively improving the repeatability of material preparation and the consistency of device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] Figure 1 Schematic diagram of chromophore photocrosslinking mechanism and curing;

[0045] Figure 2 is the thermogravimetric (TGA) curve of PCC-1;

[0046] Figure 3 is the differential thermal analysis (DSC) curve of PCC-1;

[0047] Figure 4 This is the infrared spectrum change diagram of PCC-1 after cross-linking at 365 nm for different time periods;

[0048] Figure 5 is the polarization efficiency diagram of PCC-1 film;

[0049] Figure 6 This is a statistical diagram of the temporal stability of the electro-optic coefficient at different temperatures. DETAILED DESCRIPTION

[0050] In order to make the purpose, technical solutions and advantages of the present invention more clearly understood, the present invention is further described in detail below in conjunction with the embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention. That is, the embodiments described are only part of the embodiments of the present invention, rather than all embodiments.

[0051] Therefore, the detailed description of the embodiments of the present invention provided below is not intended to limit the scope of the invention as claimed, but is merely intended to represent selected embodiments of the present invention. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative work are within the scope of protection of the present invention.

[0052] It should be noted that relational terms such as "first" and "second" are used only to distinguish one entity or operation from another entity or operation, and do not necessarily require or imply any actual relationship or order between these entities or operations. Moreover, the terms "comprises," "comprising," or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or apparatus comprising a series of elements includes not only those elements, but also other elements not explicitly listed, or elements inherent to such process, method, article, or apparatus. In the absence of further limitations, an element defined by the phrase "comprising a ..." does not exclude the presence of other identical elements in the process, method, article, or apparatus comprising the element.

[0053] The features and performance of the present invention are further described in detail below with reference to the embodiments and drawings.

[0054] Example

[0055] An organic electro-optical material that can be used for waveguide interface functionalization has the following structural formula:

[0056]

[0057] The preparation process of the above-mentioned organic electro-optical material that can be used for waveguide interface functionalization is as follows:

[0058]

[0059] Its specific preparation method is:

[0060] (1) Sodium ethoxide solution was added to a mixture of an electron donor aldehyde (compound 1) and an isophorone derivative, heated to 65°C for reaction, and refluxed overnight. After the reaction was completed, the solvent was removed by rotary evaporation, and the mixture was extracted with ethyl acetate three times and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography to obtain compound 2, which was used directly in the next reaction without further purification.

[0061] (2) Compound 2 was dissolved in anhydrous N,N-dimethylformamide, and then 2.2 equivalents of tert-butyldimethylsilyl chloride and 2.4 equivalents of imidazole were added. The reaction was stirred at room temperature overnight. After completion, the mixture was poured into water and extracted with ethyl acetate three times. The mixture was washed with concentrated brine and dried over magnesium sulfate. The crude product was purified by column chromatography to obtain orange-red compound 3 with a yield of 63.2%. MS (ESI) (M+, C 54 H 67 NO3SSi2): 865.41;

[0062] (3) 2.0 equivalents of diethyl cyanomethylphosphonate were slowly added to a tetrahydrofuran solution of sodium hydride under ice bath, and stirring was continued after the addition was complete to obtain a clear solution; an anhydrous tetrahydrofuran solution of compound 3 was added to the clear solution, and the reaction was refluxed overnight under a protective atmosphere. After the reaction was completed, water was added to quench the solution, and the mixture was extracted with ethyl acetate three times and dried over magnesium sulfate. The mixture was purified by silica gel chromatography and eluted with a mixed solvent of ethyl acetate and hexane to obtain an orange-yellow compound 4 with a yield of 45.6%. MS (ESI) (M+, C 56 H 68 N2O2SSi2):888.40;

[0063] (4) At -78°C under a protective atmosphere, 1.2 equivalents of diisobutylaluminum hydride in hexane was slowly added to a toluene solution of 1.78 g of compound 4. After reacting at -78°C for 2 h, water-wet silica gel was added. After returning to room temperature, stirring was continued for 2 h. After the hydrolysis was completed, the filtrate was filtered and the solvent was evaporated. The filtrate was purified by silica gel chromatography and eluted with a mixed solvent of ethyl acetate and hexane to obtain an orange-red compound 5 with a yield of 76.2%. MS (ESI) (M+, C 56 H 69 NO3SSi2): 891.43;

[0064] (5) 1.5 equivalents of tetrabutylammonium fluoride solution were gradually added dropwise to the tetrahydrofuran solution of compound 5. After reacting at room temperature for 0.5 h, the mixture was poured into water and extracted with ethyl acetate three times. The mixture was dried with magnesium sulfate and the solvent was dried by rotary evaporation to obtain the orange-red compound 6. The next step of the reaction was carried out without purification. The yield was 95.2%. MS (ESI) (M+, C 24 H 33 NO3S): 415.20;

[0065] (6) 2.4 equivalents of 4-azido-2,3,5,6-tetrafluorobenzoic acid, 3.0 equivalents of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) and a catalytic amount of 4-dimethylaminopyridine (DMAP) were dissolved in anhydrous dichloromethane to react and obtain a clear solution. A dichloromethane solution of compound 6 was added to the solution and the temperature was raised to room temperature for overnight reaction. After the reaction was completed, the solution was poured into water and extracted with ethyl acetate three times. The product was dried over anhydrous magnesium sulfate and the crude product was purified by column chromatography to obtain an orange-red compound 7 with a yield of 81.4%. MS (ESI) (M+, C 38 H 31 F8N7O5S): 849.12;

[0066] (7) 0.89 g of compound 7 and 0.53 g of electron acceptor were dissolved in 10 mL of anhydrous ethanol and heated to 75 °C for 1 h. The solvent was removed by rotary evaporation and the crude product was purified by column chromatography to obtain electro-optical chromophore compound PCC-1 with a yield of 54%. MS (ESI) (M+, C 58 H 42 F 12 N 12 O9S): 1310.27.

[0067] Test example

[0068] 1. Solution preparation and thin film deposition

[0069] The prepared electro-optical material can be well dissolved in common solvents such as cyclopentanone and 1,1,2-trichloroethane (TCE). It can be deposited into uniform and dense electro-optical films on various substrates such as silicon waveguides, silicon nitride waveguides, optical fibers, gold electrodes, HfO2, and TiO2 through low-cost methods such as spin coating and doctor blade coating. The specific preparation method is as follows:

[0070] 100 mg of the electro-optical material was weighed and added to 1.15 g of TCE. The mixture was sealed and stirred overnight. The mixture was then filtered through a 0.2 μm filter membrane and the filtrate was allowed to stand for 30 minutes to obtain a uniform polymer solution with a mass fraction of 8%. Thin films were prepared by spin coating. 100 μL of the polymer solution was pipetted onto a 1 cm × 1 cm substrate and spun at 400 rpm for 1 minute. After spin coating, the film was heated on a 70°C hot plate for 5 minutes to remove most of the solvent. The film was then transferred to a vacuum drying oven and dried overnight. The final film thickness was approximately 1 μm.

[0071] 2. Polarization treatment and photocrosslinking curing

[0072] The dried film needs to be electric field polarized to impart electro-optical properties. The polarization adopts the contact polarization method, and the applied electric field strength ranges from 20 to 100 V / μm. After polarization, photocrosslinking is carried out using a 365 nm UV lamp. Depending on the thickness of the film, the UV light power density is set to 3-5 mW / cm², and the irradiation time is 5.0-10 minutes. The change in glass transition temperature is monitored by differential thermal analysis, and the crosslinking completion standard is when the glass transition temperature rises to above 150°C to ensure that the film is fully crosslinked and cured. The entire photocrosslinking process needs to be carried out under nitrogen protection to avoid oxygen affecting the crosslinking reaction. After crosslinking, the glass transition temperature of the electro-optic polymer increases significantly, while the solvent tolerance and mechanical strength are enhanced. The unexposed area can be removed with solvents such as chloroform to obtain a cross-linked electro-optical film with a clear structure at the specified location. The mechanism of cross-linking and curing and the schematic diagram of the cross-linking process are shown in Figure 1After photo-crosslinking and curing, the thermal decomposition temperature of the material tested by thermogravimetric analyzer (TGA) was higher than 250℃ ( Figure 2 ). The T of the material was tested using a differential thermal analyzer. g Above 150℃( Figure 3 During the cross-linking process, the infrared characteristic peak of the -N3 structure gradually disappears. Figure 4 The display is at 5mW / cm 2 Under the light power, the intensity of the -N3 infrared absorption peak changes with time. After 6 minutes of irradiation, the absorption peak almost disappears, indicating that the cross-linking is completed.

[0073] 3. Electro-optical performance test

[0074] The electro-optic coefficient of the cross-linked electro-optic film was measured using the Teng-Man reflection method. The test results and polarization efficiency analysis are shown in the figure. Figure 5 By plotting the variation of the electro-optic coefficient with the polarization electric field intensity and calculating its slope, the polarization efficiency of the material can be obtained. This parameter is used to evaluate the electro-optical response ability of the material under the same polarization field intensity conditions with different chromophore concentrations. Figure 5 The results show that the maximum electro-optic coefficient of this electro-optic material can reach 308 pm / V.

[0075] 4. Thermal stability test

[0076] To evaluate the thermal stability of the cross-linked electro-optical film, long-term storage experiments were conducted under different temperature conditions, including:

[0077] 1) Place at 85°C (nitrogen protection) for 1000 hours;

[0078] 2) Place at 100°C (nitrogen protection) for 1000 hours;

[0079] 3) Place at 120°C (nitrogen protection) for 1000 hours;

[0080] 4) Heat the device to 120°C under nitrogen protection, keep it warm for 1 hour, then cool it to 0°C, reheat it to 120°C and keep it warm for 1 hour. The heating and cooling rate is 10°C / min. Repeat this cycle 100 times.

[0081] The test results are as follows Figure 6 Experimental data shows that after 1000 hours in an 85°C environment, the electro-optic coefficient remains above 99% of its initial value; after aging at 100°C for 1000 hours, the electro-optic coefficient still remains above 95%. Even after 1000 hours of storage at 120°C, the electro-optic activity still remains above 90%, demonstrating the material's excellent thermal stability.

[0082] After 100 heating / cooling cycles, microscopic observation showed no cracks on the film surface, and no warping or delamination between the film and the device, indicating a strong bond, demonstrating high bonding strength between the electro-optical material and the waveguide interface.

[0083] In summary, the organic electro-optic polymer material prepared in this embodiment can be integrated with micro-nano photonic devices through low-cost processing technology, and can be photocrosslinked and cured at room temperature, giving it excellent electro-optical performance and high-temperature stability.

Claims

1. An organic electro-optical material that can be used for waveguide interface functionalization, characterized in that: Its structural formula is as follows: Mode ; Wherein, X is one of O and S atoms; R1: C1-C10 alkyl, or one of the following groups: ； R2: C1-C10 linear or branched alkyl, or one of the following groups: ； R3: C1-C10 linear or branched alkyl, or one of the following groups: 。 2. The method for preparing an organic electro-optical material that can be used for waveguide interface functionalization according to claim 1, characterized in that: The following steps are included: and an electron acceptor were dissolved in anhydrous ethanol, heated to 75°C for 1 h, and then the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain the product; Among them, the formula The compound structural formula is as follows: Mode .

3. The method for preparing an organic electro-optical material that can be used for waveguide interface functionalization according to claim 2, wherein: Mode The preparation method of the compound comprises the following steps: (1) Sodium ethoxide solution was added to a mixture of an electron donor and an isophorone derivative, heated to 65°C for reaction, and refluxed overnight. After the reaction was completed, the solvent was removed by rotary evaporation, and the mixture was extracted with ethyl acetate three times and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography to obtain compound 2; (2) Compound 2 was dissolved in anhydrous N,N-dimethylformamide, and then tert-butyldimethylsilyl chloride and imidazole were added. The reaction was stirred at room temperature overnight. After completion, the mixture was poured into water and extracted with ethyl acetate. The mixture was washed with concentrated brine and dried over magnesium sulfate. The crude product was purified by column chromatography to obtain an orange-red compound 3. (3) Add diethyl cyanomethylphosphate dropwise to a tetrahydrofuran solution of sodium hydride under ice bath, continue stirring after the addition is complete, and obtain a clear solution; add an anhydrous tetrahydrofuran solution of compound 3 to the clear solution, and reflux overnight under a protective atmosphere. After the reaction is complete, quench with water, extract with ethyl acetate, dry with magnesium sulfate, and purify by silica gel chromatography, eluting with a mixed solvent of ethyl acetate and hexane to obtain an orange-yellow compound 4; (4) At -78°C under a protective atmosphere, a hexane solution of diisobutylaluminum hydride was slowly added to a toluene solution of compound 4. After reacting at -78°C for 2 h, water-wet silica gel was added, and the mixture was returned to room temperature and stirred for 2 h. After the hydrolysis was completed, the filtrate was filtered, the solvent was evaporated, and the filtrate was purified by silica gel chromatography, eluting with a mixed solvent of ethyl acetate and hexane to obtain an orange-red compound 5. (5) Tetrabutylammonium fluoride solution was added dropwise to the tetrahydrofuran solution of compound 5, reacted at room temperature for 0.5 h, poured into water, extracted with ethyl acetate three times, dried over magnesium sulfate, and the solvent was dried to obtain orange-red compound 6; (6) 4-azido-2,3,5,6-tetrafluorobenzoic acid, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and 4-dimethylaminopyridine were dissolved in anhydrous dichloromethane to react and obtain a clear solution; a dichloromethane solution of compound 6 was added to the solution, and the temperature was raised to room temperature and reacted overnight. After the reaction was completed, the solution was poured into water, extracted with ethyl acetate three times, and dried over anhydrous magnesium sulfate. The crude product was purified by column chromatography to obtain an orange-red compound 7, which is the formula compound.

4. The method for preparing an organic electro-optical material for waveguide interface functionalization according to claim 2, wherein: The electron acceptor structure is as follows As shown: Mode .

5. The method for preparing an organic electro-optical material that can be used for waveguide interface functionalization according to claim 3, wherein: The electron donor structure in step (1) is as follows: As shown: Mode .

6. Use of the organic electro-optical material for waveguide interface functionalization according to claim 1 in the preparation of electro-optical thin film materials for optoelectronic devices.

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