Derivatives of organic electroluminescent diode light-emitting layer host materials and methods for their synthesis

Abstract

This invention provides a class of organic light-emitting diode (OLED) host material derivatives and their synthesis methods. Specifically, the host material derivatives have the structure shown in Formula I, and the host material can be derivatized through a high-valent iodine reagent C-H bond functionalization reaction to obtain host material derivatives with different functional group modifications.

Description

Technical Field

[0001] This invention relates to the field of materials chemistry. Specifically, this invention provides a novel organic light-emitting diode (OLED) light-emitting layer host material derivative and a corresponding synthesis method. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a novel electroluminescent device with a multilayer ultrathin film structure, exhibit significant advantages over the previous generation of liquid crystal displays (LCDs), including low power consumption, wide viewing angle, high color gamut, fast response, and lightweight ultrathin design. Currently, OLEDs are gradually replacing LCDs in displays and lighting, possessing considerable development potential. However, most electrophosphorescent materials suffer from severe concentration quenching and triplet-triplet annihilation, which is detrimental to device performance. Research indicates that dispersing phosphorescent materials as guest materials within the host material can effectively suppress concentration quenching and triplet-triplet annihilation, thereby improving device performance. In this host-guest doping system, the host material must possess a higher bandgap and triplet energy level than the luminescent guest material to ensure efficient energy transfer to the guest material and promote luminescence. Currently, aromatic phosphorus oxides are widely used in host materials due to their large bandgap and high triplet energy level. However, excessively high triplet energy levels can hinder the injection and transport of electrons and holes, leading to problems such as high driving voltage and severe efficiency roll-off in devices using these materials. Therefore, derivatization modification of aromatic phosphorus oxide host materials, by introducing different functional groups to regulate the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), and triplet energy levels, holds promise for obtaining highly efficient host materials and opening up new avenues for improving the overall performance of OLED devices.

[0003] Currently, methods for derivatizing aromatic phosphorus oxides are relatively limited. The main derivatization route involves bromination or iodization followed by transition metal-catalyzed coupling reactions to modify the molecular structure. This method has the following problems: 1) Bromination and iodization reactions have poor site selectivity and low yields; 2) Monohalogenated and dihalogenated products have similar polarities and are difficult to separate; 3) When using transition metal-catalyzed coupling reactions for post-modification, the types of functional groups that can be introduced are limited, and transition metal residues may remain after the reaction, affecting device lifespan.

[0004] Therefore, there is an urgent need to develop a method for obtaining aromatic phosphorus oxide derivatization and modification host materials with high selectivity and high yield. Summary of the Invention

[0005] The purpose of this invention is to provide a method for obtaining aromatic phosphorus oxide derivatives in high selectivity and high yield. This method involves derivatizing aromatic phosphorus oxide host materials through a high-valent iodine reagent C-H bond functionalization reaction. By introducing different functional groups, the HOMO, LUMO, and triplet energy levels of the molecule can be controlled, allowing for the selection of highly efficient host materials and improving the overall performance of OLED devices. The high-valent iodine reagent is simple to prepare, operates under mild reaction conditions, is recyclable, and can obtain products with various functional groups with high selectivity and high yield.

[0006] In a first aspect of the present invention, a compound of formula I is provided:

[0007]

[0008] Among them, X is selected from the following groups: O, S;

[0009] R1 is selected from the following groups: -SCN, -SeCN, -NO2, -L-Rx;

[0010] The Rx is selected from substituted or unsubstituted groups selected from the group consisting of: C1-C18 alkyl, C3-C18 saturated or unsaturated cycloalkyl, C6-C30 aromatic ring, 5-30 membered heteroaromatic ring, 5-30 membered heterocycle, C3-C30 carbon ring,

[0011]

[0012] The -L- is selected from the following group: -O-, -S-, -NRa-, -SO2-, -SO2-O-, -O-SO2-, -SO2-NH-, -C=O-, -COO-, -OC=O-;

[0013] The Ra is selected from the group consisting of: H, substituted or unsubstituted C1-C6 alkyl groups; or Ra together with any substituent on N or Rx and the atoms attached thereto to form a substituted or unsubstituted 3-8 membered ring; the Rc and Rd are selected from the group consisting of: substituted or unsubstituted C6-C30 aromatic rings, substituted or unsubstituted 5-30 membered heteroaromatic rings.

[0014] The substitution mentioned therein refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of: deuterium, tritium, halogen, oxo, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, and C3-C8 cycloalkyl.

[0015] Unless otherwise specified, the heterocyclic rings and heterocycles include 1, 2, 3, or 4 heteroatoms selected from the group consisting of N, S, and O.

[0016] In another preferred embodiment, R1 is selected from the group consisting of: -SCN, -SeCN, -NO2, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C1-C18 alkylthio, -O-substituted or unsubstituted C6-C20 aromatic ring, -O-substituted or unsubstituted 5-20 membered heteroaromatic ring, -S-substituted or unsubstituted C6-C20 aromatic ring, -S-substituted or unsubstituted 5-20 membered heteroaromatic ring, -NRa-substituted or unsubstituted C1-C18 alkyl, -NRa-substituted or unsubstituted C6-C20 aromatic ring, -NRa-substituted or unsubstituted 5-20 membered heteroaromatic ring, -SO2-substituted or unsubstituted C1-C18 alkyl, -SO2-substituted or unsubstituted C6-C20 aromatic ring, -SO2-substituted or unsubstituted Substituted 5-20-membered heteroaromatic rings, -O-SO2-substituted or unsubstituted C6-C20 aromatic rings, -O-SO2-substituted or unsubstituted 5-20-membered heteroaromatic rings, -SO2-O-substituted or unsubstituted C1-C18 alkyl groups, -SO2-O-substituted or unsubstituted C6-C20 aromatic rings, -SO2-O-substituted or unsubstituted 5-20-membered heteroaromatic rings, -COO-substituted or unsubstituted C1-C18 alkyl groups, -COO-substituted or unsubstituted C6-C20 aromatic rings, -COO-substituted or unsubstituted 5-20-membered heteroaromatic rings, -OC=O-substituted or unsubstituted C1-C18 alkyl groups, -OC=O-substituted or unsubstituted C6-C20 aromatic rings, -OC=O-substituted or unsubstituted 5-20-membered heteroaromatic rings,

[0017] Ra is defined as described above;

[0018] The substitution refers to the substitution of one or more hydrogen atoms on a group by a substituent selected from the group consisting of: deuterium, tritium, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, and halogenated C1-C4 alkoxy.

[0019] In another preferred embodiment, X is 0.

[0020] In another preferred embodiment, the compound is selected from the group consisting of:

[0021]

[0022]

[0023] A second aspect of the invention provides a method for preparing a compound as described in the first aspect of the invention, the method comprising:

[0024] (1) The main material was reacted with a high-valent iodine reagent to obtain a diaryl high-iodine salt intermediate;

[0025] (2) The diaryl highiodide salt intermediate obtained in the previous step is reacted with a nucleophile to obtain the host material derivative as described in the first aspect of the present invention;

[0026] The main material described herein has a structure as shown in Formula II:

[0027]

[0028] Where X is selected from the following groups: O, S;

[0029] The high-valent iodine reagent is selected from the following group: High-priced iodine reagent 1 High-valent iodine reagent 2, or a combination thereof;

[0030] The nucleophile is selected from the group consisting of: TMSCF3, TMSCF2H, KSCN, KSeCN, NaNO2, substituted or unsubstituted Nu-OH, substituted or unsubstituted Nu-SH, substituted or unsubstituted Nu-NRaH, substituted or unsubstituted Nu-SO2Na, substituted or unsubstituted Nu-SO2-ONa, substituted or unsubstituted Nu-COOH. The Nu is selected from the group consisting of: C1-C18 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and 5-30 heteroaryl.

[0031] Ra is selected from the following group: H, C1-C6 alkyl, halo-C1-C6 alkyl;

[0032] The substitution refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of: deuterium, tritium, halogen, oxo, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, and C3-C8 cycloalkyl.

[0033] In another preferred embodiment, the method has one or more features selected from the group consisting of:

[0034] (a) The reaction temperature in step (1) is -80 to 120°C;

[0035] (b) The reaction time for step (1) is 1 to 48 hours;

[0036] (c) The ratio of the main material to the high-valent iodine reagent in step (1) is 1:(0.1-5);

[0037] (d) The solvent in step (1) is selected from the group consisting of acetonitrile, dichloromethane, trifluoroethanol, hexafluoroisopropanol, trifluoroacetic acid, trifluoromethanesulfonic acid, hexafluorobenzene, chlorobenzene, bromobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, o-dibromobenzene, m-dibromobenzene, p-dibromobenzene, nitrobenzene, or combinations thereof.

[0038] In another preferred embodiment, the solvent in step (1) is a mixed solution of trifluoromethanesulfonic acid and trifluoroacetic acid.

[0039] In another preferred embodiment, the solvent in step (1) is a mixed solvent of TFA / TfOH = 10 / 1.

[0040] In another preferred embodiment, the ratio of the mixed solvents in step (1) is a weight ratio or a volume ratio.

[0041] In another preferred embodiment, the reaction temperature of step (1) is 10-50°C.

[0042] In another preferred embodiment, the reaction time of step (1) is 12-36 h.

[0043] In another preferred embodiment, the ratio of the main material to the high-valent iodine reagent in step (1) is 1:(0.5-1.5).

[0044] In another preferred embodiment, step (1) further includes: after the reaction is complete, the reaction solution is concentrated, dissolved in a small amount of MeOH, and then dropped into n-hexane to precipitate, and filtered to obtain the diaryl highiodine salt intermediate.

[0045] In another preferred embodiment, step (2) is carried out in the presence of an additive selected from the group consisting of diethylamine, triethylamine, DBU, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, sodium trifluoromethanesulfonate, cuprous chloride, cuprous bromide, cuprous iodide, or combinations thereof.

[0046] In another preferred embodiment, the additive is cesium carbonate.

[0047] In another preferred embodiment, the method has one or more features selected from the group consisting of:

[0048] (a) The reaction temperature in step (2) is -80 to 120°C;

[0049] (b) The reaction time in step (2) is 1 to 48 hours;

[0050] (c) The ratio of the diaryl highiodine salt intermediate to the nucleophilic reagent in step (2) is 1:(1-8);

[0051] (d) The solvent in step (2) is selected from the group consisting of n-hexane, cyclohexane, carbon tetrachloride, benzene, toluene, o-xylene, m-xylene, p-xylene, ethyl acetate, 1,2-dichloroethane, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, or combinations thereof.

[0052] In another preferred embodiment, the solvent in step (2) is toluene.

[0053] In another preferred embodiment, the reaction temperature in step (2) is 100-150°C.

[0054] In another preferred embodiment, the reaction time of step (2) is 12-36 h.

[0055] In another preferred embodiment, the ratio of the diaryl highiodine salt intermediate to the nucleophilic reagent in step (2) is 1:(1-3).

[0056] It should be understood that, within the scope of this invention, the above-described technical features of this invention and the technical features specifically described below (such as in the embodiments) can be combined with each other to form new or preferred technical solutions. Due to space limitations, they will not be described in detail here. Attached Figure Description

[0057] Figure 1 The 1H NMR spectrum of S1-21, a derivative of aromatic phosphorus oxides. Detailed Implementation

[0058] Through extensive and in-depth research, and through numerous screenings and tests, the inventors have developed a method for obtaining aromatic phosphorus oxide host materials with high selectivity and high yield. This method involves a high-valent iodine reagent based on the 3,5-dimethyl-4-iodoisoxazole group reacting with the aromatic phosphorus oxide host material via a C-H bond functionalization reaction, thereby yielding various functionalized products. The high-valent iodine reagent, as an electrophilic arylating agent, possesses wide applicability, non-toxicity, and environmental friendliness. The preparation method of the high-valent iodine reagent exhibits mild conditions, a simple operation process, low preparation cost, and the advantage of recyclability. When using the high-valent iodine reagent for C-H bond functionalization, the 3,5-dimethyl-4-iodoisoxazole group, as an excellent non-transfer group, can obtain various functionalized products with high selectivity and high yield. The reaction operation is simple and convenient, with a wide range of applications, and can serve as an effective tool for the derivatization and modification of aromatic phosphorus oxide host materials. This invention is based on this foundation.

[0059] High-priced iodine reagent

[0060] In previous research, the inventors successfully developed a high-valent iodine reagent based on the 3,5-dimethyl-4-iodoisoxazole group, which, as an electrophilic arylation reagent, possesses the characteristics of wide applicability, non-toxicity, and no transition metal residue. The preparation method of this reagent exhibits mild conditions, simple operation procedures, low preparation costs, and the advantage of recyclability. When using this high-valent iodine reagent to derivatize substrates, a diaryl high-iodine salt intermediate is directly obtained through C-H bond functionalization, followed by reaction with the corresponding nucleophile. In aryl transfer reactions, the 3,5-dimethyl-4-iodoisoxazole group, as an excellent non-transfer group, ensures highly selective coupling reactions between the aryl phosphorus oxide moiety and the nucleophile, enabling diverse modifications to its molecular structure and achieving coupling reactions that are difficult to achieve with transition metal catalysis. Therefore, this high-valent iodine reagent has the potential to become an effective tool for the derivatization modification of aromatic phosphorus oxide host materials.

[0061] Preparation of aromatic phosphorus-oxygen host material derivatives of chemical formula I

[0062] The first step is the preparation of the diaryl highiodine salt intermediate.

[0063]

[0064] Where X represents O and S.

[0065] The specific procedure is as follows: High-valent iodine reagent (1 mmol) and the main material (1 mmol) are added sequentially to a solvent (5 mL). The reaction temperature is -80 to 120 °C, and the reaction time is 1 to 24 h. After confirming the complete reaction by TLC, the reaction solution is evaporated to dryness. The solution is dissolved in a small amount of MeOH and then added dropwise to n-hexane for precipitation. The intermediate, a diaryl high-iodine salt, is obtained by filtration.

[0066] The solvent is selected from the group consisting of acetonitrile, dichloromethane, trifluoroethanol, hexafluoroisopropanol, trifluoroacetic acid, trifluoromethanesulfonic acid, hexafluorobenzene, chlorobenzene, bromobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, o-dibromobenzene, m-dibromobenzene, p-dibromobenzene, nitrobenzene, or combinations thereof. Preferably, the solvent is trifluoroformic acid.

[0067] The high-valent iodine reagents were selected from the following group: High-priced iodine reagent 1 High-valent iodine reagent 2, or a combination thereof.

[0068] The second step is the subsequent functionalization reaction of the diaryl highiodide salt intermediate.

[0069]

[0070] Where X represents O and S.

[0071] The specific procedure is as follows: Add the diaryl highiodide intermediate (1 mmol) obtained in the first step and the nucleophile (Nu) to the solvent (5 ml) in sequence. - Alternatively, NuH (1.5 mmol) and an additive (2 mmol) were added, and the reaction was carried out at -80 to 120 °C for 1 to 24 h. After confirming the complete reaction by TLC, the reaction solution was evaporated to dryness. The solid product was obtained by silica gel column chromatography.

[0072] The nucleophile is selected from the following group: KSCN, KSeCN, NaNO2, C1-C18 substituted or unsubstituted alkyl alcohols, C1-C18 substituted or unsubstituted alkyl thiols, substituted or unsubstituted C6-C30 arylphenols, substituted or unsubstituted 5-30 heteroarylphenols, substituted or unsubstituted C6-C30 arylthiophenols, substituted or unsubstituted 5-30 heteroarylthiophenols, substituted or unsubstituted C1-C18 alkylamines, substituted or unsubstituted C6-C30 arylamines, substituted or unsubstituted 5-30 heteroarylamines, substituted or unsubstituted C1-C18 alkyl sulfinates, substituted or unsubstituted C6-C30 aryl sulfinates. Sodium sulfinate, sodium sulfinate of substituted or unsubstituted 5-30-membered heteroaryl groups, sodium sulfonate of substituted or unsubstituted C1-C18 alkyl sulfonate, sodium sulfonate of substituted or unsubstituted C6-C30 aryl groups, sodium sulfonate of substituted or unsubstituted 5-30-membered heteroaryl groups, sodium sulfonate of substituted or unsubstituted C1-C18 alkyl carboxylic acid, sodium sulfonate of substituted or unsubstituted C6-C30 aryl carboxylic acid, sodium sulfonate of substituted or unsubstituted 5-30-membered heteroaryl carboxylic acid, sodium sulfonate of substituted or unsubstituted diC6-C30 aryl phosphate, sodium sulfonate of substituted or unsubstituted di5-30-membered heteroaryl phosphate, sodium sulfonate of substituted or unsubstituted diC6-C30 aryl phosphate, sodium sulfonate of substituted or unsubstituted di5-30-membered heteroaryl phosphate, or combinations thereof.

[0073] When the nucleophile is an amine, diphenylamine and its derivatives, and diaryleneamine and its derivatives are excluded.

[0074] The solvent is selected from the group consisting of: n-hexane, cyclohexane, carbon tetrachloride, benzene, toluene, o-xylene, m-xylene, p-xylene, ethyl acetate, 1,2-dichloroethane, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, or combinations thereof.

[0075] The additives are selected from the following group: none, diethylamine, triethylamine, DBU, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, sodium trifluoromethanesulfonate, cuprous chloride, cuprous bromide, cuprous iodide, or combinations thereof.

[0076] the term

[0077] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains.

[0078] As used herein, when referring to a specific enumerated value, the term “about” means that the value can vary by no more than 1% from the enumerated values. For example, as used herein, the expression “about 100” includes all values ​​between 99 and 101 (e.g., 99.1, 99.2, 99.3, 99.4, etc.).

[0079] As used herein, the terms “containing” or “including (comprise)” can be open-ended, semi-closed, or closed. In other words, the terms also include “consistently made of” or “composed of”.

[0080] As used herein, the term “room temperature” or “normal temperature” refers to a temperature of 4–40°C, preferably 25 ± 5°C.

[0081] As used herein, the term “C1-C6 alkyl” refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, or similar groups, and “C1-C4 alkyl” has a similar definition.

[0082] The term "C6-C30 aryl" refers to an aryl group having 6 to 30 carbon atoms, including monocyclic or bicyclic aryl groups, such as phenyl, thioyl, or similar groups.

[0083] The term "5-30 heteroaryl" refers to a heteroaryl group having 5-30 ring atoms (including 1-10 heteroatoms and the remaining carbon atoms), such as pyridyl, pyrimidinyl, furanyl, or similar groups.

[0084] The term "5-30 cyclic group" refers to a heterocyclic group (including fully saturated or partially unsaturated cases) with 8-30 ring atoms (including 1-10 heteroatoms and the remaining carbon atoms), such as tetrahydrofuran group.

[0085] The term "halogen" refers to F, Cl, Br, and I.

[0086] The main advantages of this invention include:

[0087] (1) The reagents of the present invention are simple to prepare and easy to obtain.

[0088] (2) The main material derivatives of the present invention have many novel structures, some of which are difficult to achieve by transition metal-catalyzed coupling reactions.

[0089] (3) The synthesis method of the present invention utilizes the carbon-hydrogen bond functionalization reaction of high-valent iodine reagent. Compared with the coupling reaction catalyzed by transition metals, it does not require pre-functionalization, has a higher yield, better site selectivity, and no transition metal residue in the product.

[0090] The invention is further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. Experimental methods in the following embodiments, unless otherwise specified, are generally performed under conventional conditions, such as those described in Sambrook et al., Molecular Cloning: A Laboratory Manual (New York: Cold Spring Harbor Laboratory Press, 1989), or as recommended by the manufacturer. Unless otherwise stated, percentages and parts are by weight.

[0091] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as are familiar to those skilled in the art. Furthermore, any methods and materials similar to or equivalent to those described herein may be applied to the methods of this invention. The preferred embodiments and materials described herein are for illustrative purposes only.

[0092] abbreviations

[0093]

[0094] General Implementation

[0095] Synthesis of diaryl highiodine salt intermediates

[0096]

[0097] Where X represents O and S.

[0098] Add 1 mmol of high-valent iodine reagent and the main material, di[2-((oxo)diphenylphosphino)phenyl] ether (DPEPO, 1 mmol), sequentially to a solvent (5 mL). React at -80 to 120 °C for 1 to 24 h. After confirming complete reaction by TLC, evaporate the reaction solution to dryness. Dissolve in a small amount of MeOH and precipitate in n-hexane. Filter to obtain the diaryl high-iodine salt intermediate.

[0099] Synthetic host material derivatives

[0100]

[0101] Where X represents O and S.

[0102] Add the diaryl periodic salt intermediate (1 mmol) and the nucleophile (Nu) sequentially to the solvent (5 mL). - Alternatively, NuH (1.5 mmol) and an additive (2 mmol) were added, and the reaction was carried out at -80 to 120 °C for 1 to 24 h. After confirming the complete reaction by TLC, the reaction solution was evaporated to dryness. The derivative was obtained by silica gel column chromatography.

[0103] Example 1: Preparation of intermediate S1 of diaryl highiodine salt

[0104]

[0105] Table 1 Screening of reaction conditions

[0106] High-priced iodine reagent solvent yield High-valent iodine reagent 1 ACN NR High-valent iodine reagent 1 DCM NR High-priced iodine reagent 1 TFE / DCM = 10 / 1 NR High-valent iodine reagent 1 TFA 23 High-valent iodine reagent 1 TFA / TfOH 87 High-priced iodine reagent 2 ACN NR High-priced iodine reagent 2 DCM NR High-priced iodine reagent 2 TFE / DCM = 10 / 1 NR High-priced iodine reagent 2 TFA 21 High-priced iodine reagent 2 TFA / TfOH 76

[0107] Existing research indicates that the stronger the electron-deficient nature of the aromatic ring of the substrate, the stronger the acidity of the solvent required for the reaction, and the lower the reaction yield. For example, trifluoromethylbenzene reacts with high-valent iodine reagent 1 in a solvent with a TFA / TfOH ratio of 10 / 1 with a yield of 73%. However, m-difluoromethylbenzene reacts with high-valent iodine reagent 1 in TfOH, with a yield of only 36%.

[0108] Table 1 shows that different solvents have a significant impact on the yield of the diaryl periodoiodide intermediate S1. Overall, the stronger the acidity of the reaction solution, the higher the yield, reaching up to 87%. Although the phosphorus-oxygen double bond of DPEPO has an electron-withdrawing effect, the aromatic ring is not particularly electron-deficient due to the conjugation electron-donating effect of oxygen.

[0109] To a mixed solvent of trifluoromethanesulfonic acid and trifluoroacetic acid (10 mL), high-valent iodine reagent 1 (682 mg, 2 mmol) and 2-[2-((oxo)diphenylphosphino)phenyl] ether (1.14 g, 2 mmol) were added sequentially, and the mixture was reacted at 25 °C for 24 h. After confirming the completeness of the reaction by TLC, the reaction solution was evaporated to dryness. The solution was dissolved in a small amount of MeOH and then precipitated dropwise into n-hexane. The product was obtained by filtration (1.647 g, yield 87%). 1 H NMR(400MHz,Chloroform-d)δ7.94(d,J=9.0Hz,1H),7.87(d,J=12.3Hz,1H),7.65–7.16(m,22H),7.10(t,J=7. 5Hz,1H),6.33(dd,J=9.2,4.6Hz,1H),6.03(dd,J=8.5,4.5Hz,1H),2.51(s,3H),2.18(s,3H).LRMS(ESI):Calc for C 41 H 33 INO4P2[M-OTf] + calc.792.09,found:791.48.

[0110] Example 2: Preparation of the host material derivative S1-1

[0111]

[0112] Diaryl periodide intermediate S1 (152 mg, 0.16 mmol) and sodium phenolate (28 mg, 0.24 mmol) were added sequentially to toluene (2 ml) and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction solution was evaporated to dryness. The solid product (80 mg, yield 74%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, Methanol-d4)δ7.72–7.27(m,24H),7.17(tt,J=7.4,1.3Hz,1H),7.14–7.07(m,2H ),6.96–6.89(m,3H),6.24(dd,J=8.3,5.1Hz,1H),6.16(dd,J=9.0,5.7Hz,1H).LRMS(ESI):Calc for C 42 H 33 O4P2[M+H] + calc.663.18,found:662.62.

[0113] Example 3: Preparation of the host material derivative S1-2

[0114]

[0115] Diaryl highiodide intermediate S1 (94 mg, 0.1 mmol), p-trifluoromethoxyphenol (28 mg, 0.15 mmol), and cesium carbonate (65 mg, 0.2 mmol) were added sequentially to toluene (2 ml) and the mixture was kept at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (54 mg, yield 72%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, DMSO-d6)δ7.78–7.27(m,25H),7.18(t,J=7.5,1.3Hz,1H),7.12–6.96(m,3H),6.24–6.12(m,2H).LRMS(ESI):Calc for C 43 H 32 F3O5P2[M+H] + calc.647.16, found:646.58.

[0116] Example 4: Preparation of the host material derivative S1-3

[0117]

[0118] Diaryl periodide intermediate S1 (94 mg, 0.1 mmol), p-methylphenol (16 mg, 0.15 mmol), and cesium carbonate (65 mg, 0.2 mmol) were added sequentially to toluene (2 ml) and the mixture was kept at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (37 mg, yield 54%) was obtained by silica gel column chromatography. 1 H NMR(400MHz,DMSO-d6)δ7.81–7.22(m,27H),7.00(dd,J=13.5,3.1Hz,1H),6.94( dd,J=8.9,3.1Hz,1H),6.14(dt,J=9.1,5.0Hz,2H),2.28(s,2H).LRMS(ESI):Calc for C 43 H 35 O4P2[M+H] + calc.677.19,found:676.63.

[0119] Example 5: Preparation of the host material derivative S1-4

[0120]

[0121] Diaryl highiodide intermediate S1 (66 mg, 0.07 mmol), pentafluorophenol (19 mg, 0.105 mmol), and cesium carbonate (45 mg, 0.14 mmol) were added sequentially to toluene (2 ml) and the mixture was kept at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (51 mg, 96% yield) was obtained by silica gel column chromatography. 1 H NMR (400MHz, DMSO-d6) δ7.76–7.26(m,22H),7.16(t,J=7.5Hz,1H),7.09(dd,J=9.0,3.3H z,1H),7.04(dd,J=13.3,3.3Hz,1H),6.14(ddd,J=17.8,8.6,5.0Hz,2H).LRMS(ESI):Calc for C 42 H 28 F5O4P2[M+H] + calc.753.13,found:752.53.

[0122] Example 6: Preparation of the main material derivative S1-5

[0123]

[0124] Diaryl highiodide intermediate S1 (66 mg, 0.07 mmol), p-trifluoromethylphenol (17 mg, 0.105 mmol), and cesium carbonate (45 mg, 0.14 mmol) were added sequentially to toluene (2 ml) and the mixture was kept at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (49 mg, 95% yield) was obtained by silica gel column chromatography. 1 H NMR(400MHz,DMSO-d6)δ7.83–7.27(m,25H),7.24–7.16(m,1H),7.15–7.03(m,4H),6.25–6.12(m,2H).LRMS(ESI):Calc for C 43 H 32 F3O4P2[M+H] + calc.731.16,found:730.53.

[0125] Example 7: Preparation of the host material derivatives S1-6

[0126]

[0127] Diaryl periodide intermediate S1 (94 mg, 0.1 mmol) and p-methylaniline (16 mg, 0.15 mmol) were added sequentially to toluene (2 ml), and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (58 mg, yield 85%) was obtained by silica gel column chromatography. 1 H NMR (400MHz, DMSO-d6) δ7.78–7.05(m,25H),6.97(d,J=8.0Hz,2H),6.88(dd,J=8.8,2.9Hz,1H),6.82(d ,J=7.9Hz,2H),6.16(dd,J=8.4,5.0Hz,1H),5.94(dd,J=8.9,5.5Hz,1H),2.18(s,3H).LRMS(ESI):Calc for C 43 H 36 NO3P2[M+H] + calc.676.21,found:675.63.

[0128] Example 8: Preparation of the main material derivatives S1-7

[0129]

[0130] Diaryl periodide intermediate S1 (66 mg, 0.07 mmol) and N-methylaniline (11 mg, 0.105 mmol) were added sequentially to toluene (2 ml) and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction solution was evaporated to dryness. The solid product (41 mg, yield 86%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, Methanol-d4)δ7.73–7.22(m,26H),7.18–7.13(m,1H),7.05–6.96(m,3H),6.82(dd, J=9.0,3.0Hz,1H),6.32–6.21(m,1H),6.00(dd,J=9.0,5.8Hz,1H),3.19(s,2H).LRMS(ESI):Calc for C 43 H 36 NO3P2[M+H] + calc.676.21,found:675.63.

[0131] Example 9: Preparation of the main material derivatives S1-8

[0132]

[0133] Diaryl periodide intermediate S1 (94 mg, 0.1 mmol) and indoline (18 mg, 0.15 mmol) were added sequentially to toluene (2 ml), and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (59 mg, yield 85%) was obtained by silica gel column chromatography. 1 H NMR (400MHz, Methanol-d4) δ7.74–7.31(m,21H),7.22–7.15(m,2H),7.14–7.08(m,3H),6.98–6.91(m,1H),6.77(d,J=8.0Hz,1H),6. 71(td,J=7.4,0.9Hz,1H),6.30(dd,1H),6.12(dd,J=8.9,5.8Hz,1H),3.80(t,J=8.4Hz,2H),3.06(t,J=8.4Hz,2H).LRMS(ESI):Calc for C 44 H 36 NO3P2[M+H] + calc.688.21,found:687.68.

[0134] Example 10 Preparation of the main material derivatives S1-9

[0135]

[0136] Diaryl periodide intermediate S1 (66 mg, 0.07 mmol) and p-trifluoromethylaniline (17 mg, 0.105 mmol) were added sequentially to toluene (2 ml) and the mixture was kept at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (23 mg, yield 45%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, Methanol-d4)δ7.74–7.23(m,25H),7.15(td,J=7.5,7.0,1.7Hz,1H),7.04–6.95(m,3H), 6.82(dd,J=9.0,3.0Hz,1H),6.26(dd,J=8.3,5.2Hz,1H),6.00(dd,J=9.0,5.8Hz,1H).LRMS(ESI):Calc forC 43 H 33 F3NO3P2[M+H] + calc.730.18,found:729.53.

[0137] Example 11 Preparation of host material derivative S1-10

[0138]

[0139] Diaryl highiodide intermediate S1 (66 mg, 0.07 mmol) and sodium methanesulfonate (11 mg, 0.105 mmol) were added sequentially to toluene (2 ml) and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction solution was evaporated to dryness. The solid product (39 mg, yield 85%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, DMSO-d6)δ8.10(dd,J=12.6,2.4Hz,1H),7.85(dd,J=8.7,2.5Hz,1H),7.80–7.20( m,23H),6.41(dd,J=8.8,4.5Hz,1H),6.15(dd,J=8.2,4.5Hz,1H),3.20(s,3H).LRMS(ESI):Calc for C 37 H 31 O5P2S[M+H] + calc.649.13,found:648.52.

[0140] Example 12 Preparation of host material derivative S1-11

[0141]

[0142] Diaryl highiodide intermediate S1 (66 mg, 0.07 mmol) and sodium benzenesulfinate (17 mg, 0.105 mmol) were added sequentially to toluene (2 ml), and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction solution was evaporated to dryness. The solid product (45 mg, 90% yield) was obtained by silica gel column chromatography. 1 H NMR (400MHz, DMSO-d6) δ7.95 (dd, J=12.7, 2.5Hz, 1H), 7.89–7.36 (m, 25H), 7.34–7.27 (m,1H),7.21–7.06(m,2H),6.96(t,J=7.5Hz,1H),6.38–6.18(m,2H).LRMS(ESI):Calc for C 42 H 33 O5P2S[M+H] + calc.711.14,found:710.63.

[0143] Example 13 Preparation of host material derivative S1-12

[0144]

[0145] Diaryl highiodide intermediate S1 (66 mg, 0.07 mmol) and sodium p-toluenesulfinate (19 mg, 0.105 mmol) were added sequentially to toluene (2 ml), and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (45 mg, yield 88%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, DMSO-d6)δ7.95(dd,J=12.7,2.5Hz,1H),7.80(dd,J=8.8,2.5Hz,1H),7.75–7.65(m,4H),7.64–7.35(m,19H),7.35–7.24(m,1H) ,7.17(dt,J=7.6,4.6Hz,2H),7.04(t,J=7.5Hz,1H),6.30(dd,J=8.8,4.4Hz,1H),6.24(dd,J=8.1,4.7Hz,1H),2.40(s,3H).LRMS(ESI):Calc for C 43 H 35 O5P2S[M+H] + calc.725.16,found:724.58.

[0146] Example 14 Preparation of host material derivative S1-13

[0147]

[0148] Diaryl periodide intermediate S1 (47 mg, 0.05 mmol) and sodium p-fluorobenzenesulfinate (14 mg, 0.075 mmol) were added sequentially to toluene (2 ml), and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (30 mg, yield 82%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, DMSO-d6)δ8.01–7.88(m,3H),7.83(dd,J=8.8,2.5Hz,1H),7.76–7.65(m,2H),7.66–7.37(m,19H),7.29(tt,J=7.5, 1.2Hz,1H),7.17(dt,J=7.7,4.5Hz,2H),7.04(t,J=7.5Hz,1H),6.30(dd,J=8.8,4.4Hz,1H),6.27–6.22(m,1H).LRMS(ESI):Calc for C 42 H 32 FO5P2S[M+H] + calc.729.14,found:728.58.

[0149] Example 15 Preparation of host material derivative S1-14

[0150]

[0151] Diaryl periodide intermediate S1 (66 mg, 0.07 mmol) and 2-mercaptopyrimidine (12 mg, 0.105 mmol) were added sequentially to toluene (2 ml), and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (31 mg, yield 65%) was obtained by silica gel column chromatography. 1 H NMR(400MHz, DMSO-d6)δ8.62(d,J=4.8Hz,2H),7.74–7.29(m,25H),7.26(t,J=4.9 Hz,1H),6.26(dd,J=8.6,5.0Hz,1H),6.19(dd,J=8.2,4.6Hz,1H).LRMS(ESI):Calc for C 40 H 31 N₂O₃P₂S[M+H] + calc.681.15,found:680.63.

[0152] Example 16 Preparation of host material derivative S1-15

[0153]

[0154] Diaryl highiodide intermediate S1 (66 mg, 0.07 mmol), perfluorotert-butanol (50 mg, 0.21 mmol), and cesium carbonate (68 mg, 0.21 mmol) were added sequentially to toluene (2 ml) and the mixture was kept at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (52 mg, 92% yield) was obtained by silica gel column chromatography. 1 H NMR(400MHz,DMSO-d6)δ7.85–6.99(m,25H),6.19(dd,J=8.2,4.7Hz,1H),6.12(dd,J=8.9,5.2Hz,1H).LRMS(ESI):Calc for C 40 H 28 F9O4P2[M+H] + calc.805.12,found:804.48.

[0155] Example 17 Preparation of host material derivatives S1-16

[0156]

[0157] Diaryl periodic salt intermediate S1 (66 mg, 0.07 mmol) and sodium nitrite (7 mg, 0.105 mmol) were added sequentially to ethylene glycol dimethyl ether (2 ml), and the reaction was maintained at 100 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction solution was evaporated to dryness. The solid product (38 mg, yield 88%) was obtained by silica gel column chromatography. 1 H NMR (400MHz, DMSO-d6) δ8.31(dd,J=13.1,2.9Hz,1H),8.15(dd,J=9.1,2.9Hz,1H),7.74(dd,J=12.5,7. 5Hz,2H),7.69–7.25(m,21H),6.38(dd,J=9.1,4.6Hz,1H),6.22(dd,J=8.2,4.6Hz,1H).LRMS(ESI):Calc forC 36 H 28 NO5P2[M+H] + calc.616.14, found:615.57.

[0158] Example 18 Preparation of host material derivatives S1-17

[0159]

[0160] Diaryl periodide intermediate S1 (66 mg, 0.07 mmol), diphenylphosphine (23 mg, 0.105 mmol), and triethylamine (11 mg, 0.105 mmol) were added sequentially to toluene (2 ml) and the mixture was reacted at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (33 mg, yield 59%) was obtained by silica gel column chromatography. LRMS(ESI): Calc for C 48 H 38 O5P3[M+H] + calc.787.19,found:786.68.

[0161] Example 19 Preparation of host material derivatives S1-18

[0162]

[0163] Diaryl highiodide intermediate S1 (66 mg, 0.07 mmol) and potassium thiocyanate (10 mg, 0.105 mmol) were added sequentially to toluene (2 ml) and the mixture was kept at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction mixture was evaporated to dryness. The solid product (42 mg, 95% yield) was obtained by silica gel column chromatography. 1 H NMR (400MHz, DMSO-d6) δ7.80 (dd, J=12.6, 2.6Hz, 1H), 7.74–7.30 (m, 23H), 7.21 (dd, J=8. 2,6.6Hz,1H),6.34(dd,J=8.8,4.9Hz,1H),6.12(dd,J=8.2,4.6Hz,1H).LRMS(ESI):Calc for C 37 H 28 NO3P2S[M+H] + calc.628.12,found:627.52.

[0164] Example 20 Preparation of host material derivative S1-19

[0165]

[0166] Diaryl periodide intermediate S1 (66 mg, 0.07 mmol), benzoic acid (10 mg, 0.075 mmol), and potassium carbonate (21 mg, 0.15 mmol) were added sequentially to toluene (2 ml), and the reaction was maintained at 120 °C for 24 h. After confirming the completion of the reaction by TLC, the reaction solution was evaporated to dryness. The solid product (mg, yield %) was obtained by silica gel column chromatography. 1H NMR (400MHz, DMSO-d6) δ8.15–8.03(m,2H),7.86–7.25(m,27H),7.16(t,J=7.5Hz ,1H),6.31(dd,J=9.0,5.3Hz,1H),6.08(dd,J=8.2,4.7Hz,1H).LRMS(ESI):Calc for C 43 H 33 O5P2[M+H] + calc.691.17,found:690.53.

[0167] Device Example 1: Fabrication of a Bottom-Emitting OLED Device

[0168] This device embodiment provides an organic electroluminescent device with the following structure: substrate / ITO anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode, and its fabrication method includes the following steps:

[0169] S1. The ITO glass substrate with a coating thickness of 150nm is washed twice in distilled water and ultrasonically cleaned for 30 minutes. It is then washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning is completed, isopropanol, acetone, methanol and other solvents are ultrasonically cleaned in sequence and then dried. The substrate is then transferred to a plasma cleaning machine and cleaned for 5 minutes. It is then sent to a vapor deposition machine, where other functional layers are deposited sequentially on the substrate as the anode.

[0170] S2. Compounds HT-001 and HI-002 are introduced into a vacuum vapor deposition apparatus, and a hole injection layer with a thickness of 10 nm is formed by evaporation through the application of current to the unit. The evaporation rate ratio of HT-001 to HI-002 is 96:4. The structures of compounds HT-001 and HI-002 are as follows:

[0171]

[0172] S3. The compound HT-001 is introduced into a vacuum vapor deposition apparatus, and a hole transport layer with a thickness of 125 nm is formed by evaporation through the application of current to the unit.

[0173] S4 introduced compound EB-1 into a vacuum vapor deposition apparatus and formed an electron blocking layer with a thickness of 35 nm by evaporation through the application of an electric current to the unit. The structure of compound EB-1 is as follows:

[0174]

[0175] S5. The phosphorescent host material S1-1 and the dopant material Ir(ppy)3 are mixed and vapor-deposited at a weight ratio of 97:3 to form a light-emitting layer.

[0176] S6 introduced compound HBL-1 into a vacuum vapor deposition apparatus and formed an electron blocking layer with a thickness of 5 nm by applying an electric current to the unit for evaporation. The structure of compound HBL-1 is as follows:

[0177]

[0178] S7. Mixed vapor deposition of T-001:Liq = 1:1, with a weight ratio of T-001 to Liq of 60:40, forming an electron transport layer of thickness. The structural formulas of T-001 and Liq are as follows:

[0179]

[0180] S8, Yb is vapor-deposited to form an electron injection layer.

[0181] S9. Deposit an Al cathode on the electron injection layer to obtain an organic electroluminescent device.

[0182] Device Examples 2-19

[0183] Referring to the preparation method provided in Device Example 1 above, the phosphorescent host material S1-1 used in Device Example 1 was replaced with the phosphorescent host materials shown in Formulas S1-2 to S1-19 provided in the specification, and the corresponding organic electroluminescent devices were prepared.

[0184] Device Comparison Example 1 - Device Comparison Example 2

[0185] Referring to the preparation method provided in Device Example 1 above, the phosphorescent host material S1-1 used in Device Example 1 was replaced with the phosphorescent host material comparative compound 1 and comparative compound 2 as shown below, and the corresponding organic electroluminescent device was prepared.

[0186]

[0187] Device performance standards

[0188] The luminescence characteristics of the organic electroluminescent devices obtained in Examples 2-20 and Comparative Examples 1-2 were tested using a KEITHLEY 2400 source measurement unit and a CS-2000 spectroradiometer to evaluate the device's driving voltage, lifetime, and luminous efficiency. The results are shown in the table below.

[0189] Table 2 Device Test Results

[0190]

[0191] As can be seen from Table 2, the organic electroluminescent devices prepared using the light-emitting layer host material derivatives provided by the present invention in Examples 1-19 have improved driving voltage, luminous efficiency, or lifetime compared with the devices prepared using comparative compounds 1-2.

[0192] All documents mentioned in this invention are incorporated herein by reference as if each document were individually incorporated by reference. Furthermore, it should be understood that after reading the foregoing teachings of this invention, those skilled in the art can make various alterations or modifications to this invention, and these equivalent forms also fall within the scope defined by the appended claims.

Claims

1. A compound represented by formula I: in, X is selected from the following groups: O, S; R1 is selected from the following groups: -SCN, -SeCN, -NO2, -L-Rx; The Rx is selected from substituted or unsubstituted groups selected from the group consisting of: C1-C18 alkyl, C3-C18 saturated or unsaturated cycloalkyl, C6-C30 aromatic ring, 5-30 membered heteroaromatic ring, 5-30 membered heterocycle, C3-C30 carbon ring, The -L- is selected from the following group: -O-, -S-, -NRa-, -SO2-, -SO2-O-, -O-SO2-, -SO2-NH-, -C=O-, -COO-, -OC=O-; The Ra is selected from the group consisting of: H, substituted or unsubstituted C1-C6 alkyl groups; or Ra together with any substituent on N or Rx and the atoms attached thereto to form a substituted or unsubstituted 3-8 membered ring; the Rc and Rd are selected from the group consisting of: substituted or unsubstituted C6-C30 aromatic rings, substituted or unsubstituted 5-30 membered heteroaromatic rings. The substitution mentioned therein refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of: deuterium, tritium, halogen, oxo, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, and C3-C8 cycloalkyl. Unless otherwise specified, the heterocyclic rings and heterocycles include 1, 2, 3, or 4 heteroatoms selected from the group consisting of N, S, and O.

2. The compound according to claim 1, characterized in that, The R1 is selected from the group consisting of: -SCN, -SeCN, -NO2, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C1-C18 alkylthio, -O-substituted or unsubstituted C6-C20 aromatic ring, -O-substituted or unsubstituted 5-20 membered heteroaromatic ring, -S-substituted or unsubstituted C6-C20 aromatic ring, -S-substituted or unsubstituted 5-20 membered heteroaromatic ring, -NRa-substituted or unsubstituted C1-C18 alkyl, -NRa-substituted or unsubstituted C6-C20 aromatic ring, -NRa-substituted or unsubstituted 5-20 membered heteroaromatic ring, -SO2-substituted or unsubstituted C1-C18 alkyl, -SO2-substituted or unsubstituted C6-C20 aromatic ring, -SO2-substituted or unsubstituted 5 5-20 membered heteroaromatic rings, -O-SO2-substituted or unsubstituted C6-C20 aromatic rings, -O-SO2-substituted or unsubstituted 5-20 membered heteroaromatic rings, -SO2-O-substituted or unsubstituted C1-C18 alkyl groups, -SO2-O-substituted or unsubstituted C6-C20 aromatic rings, -SO2-O-substituted or unsubstituted 5-20 membered heteroaromatic rings, -COO-substituted or unsubstituted C1-C18 alkyl groups, -COO-substituted or unsubstituted C6-C20 aromatic rings, -COO-substituted or unsubstituted 5-20 membered heteroaromatic rings, -OC=O-substituted or unsubstituted C1-C18 alkyl groups, -OC=O-substituted or unsubstituted C6-C20 aromatic rings, -OC=O-substituted or unsubstituted 5-20 membered heteroaromatic rings, Ra is defined as described in claim 1; The substitution refers to the substitution of one or more hydrogen atoms on a group by a substituent selected from the group consisting of: deuterium, tritium, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, and halogenated C1-C4 alkoxy.

3. The compound according to claim 1, characterized in that, X is O.

4. The compound according to claim 1, characterized in that, The compounds are selected from the group consisting of:

5. The method for preparing the compound according to claim 1, characterized in that, The method includes: (1) The main material was reacted with a high-valent iodine reagent to obtain a diaryl high-iodine salt intermediate; (2) The diaryl highiodide salt intermediate obtained in the previous step is reacted with a nucleophile to obtain the host material derivative as described in claim 1; The main material described herein has a structure as shown in Formula II: Where X is selected from the following groups: O, S; The high-valent iodine reagent is selected from the following group: High-priced iodine reagent 1 High-valent iodine reagent 2, or a combination thereof; The nucleophile is selected from the group consisting of: TMSCF3, TMSCF2H, KSCN, KSeCN, NaNO2, substituted or unsubstituted Nu-OH, substituted or unsubstituted Nu-SH, substituted or unsubstituted Nu-NRaH, substituted or unsubstituted Nu-SO2Na, substituted or unsubstituted Nu-SO2-ONa, substituted or unsubstituted Nu-COOH. The Nu is selected from the group consisting of: C1-C18 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, and 5-30 heteroaryl. Ra is selected from the following group: H, C1-C6 alkyl, halo-C1-C6 alkyl; The substitution refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of: deuterium, tritium, halogen, oxo, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C2-C4 alkenyl, C2-C4 alkynyl, and C3-C8 cycloalkyl.

6. The preparation method according to claim 5, characterized in that, The method has one or more features selected from the following group: (a) The reaction temperature in step (1) is -80 to 120°C; (b) The reaction time for step (1) is 1 to 48 hours; (c) The ratio of the main material to the high-valent iodine reagent in step (1) is 1:(0.1-5); (d) The solvent in step (1) is selected from the group consisting of acetonitrile, dichloromethane, trifluoroethanol, hexafluoroisopropanol, trifluoroacetic acid, trifluoromethanesulfonic acid, hexafluorobenzene, chlorobenzene, bromobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, o-dibromobenzene, m-dibromobenzene, p-dibromobenzene, nitrobenzene, or combinations thereof.

7. The preparation method according to claim 5, characterized in that, The solvent in step (1) is a mixture of trifluoromethanesulfonic acid and trifluoroacetic acid.

8. The preparation method according to claim 5, characterized in that, Step (2) is carried out in the presence of an additive selected from the group consisting of: diethylamine, triethylamine, DBU, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, sodium trifluoromethanesulfonate, cuprous chloride, cuprous bromide, cuprous iodide, or combinations thereof.

9. The preparation method according to claim 5, characterized in that, The method has one or more features selected from the following group: (a) The reaction temperature in step (2) is -80 to 120°C; (b) The reaction time in step (2) is 1 to 48 hours; (c) The ratio of the diaryl highiodine salt intermediate to the nucleophilic reagent in step (2) is 1:(1-8); (d) The solvent in step (2) is selected from the group consisting of n-hexane, cyclohexane, carbon tetrachloride, benzene, toluene, o-xylene, m-xylene, p-xylene, ethyl acetate, 1,2-dichloroethane, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, or combinations thereof.

10. The preparation method according to claim 9, characterized in that, The solvent is toluene.

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