Organic chiral auxiliary functional material as well as preparation method and application thereof

Abstract

The invention provides a series of organic chiral micromolecule auxiliary functional materials which can be applied to main body materials, electron transport materials or hole transport materials of functional layers in circular polarization organic light-emitting diodes, and belongs to the technical field of organic electroluminescent materials. According to the invention, chiral oxazoline, chiral binaphthyl, chiral spiro, chiral paracyclophane and chiral 1, 2-cyclohexanediamine are used as chiral construction units, and are introduced into main body, electron or hole transport material molecules to construct a series of chiral compounds containing chiral oxazoline, chiral binaphthyl, chiral spiro, chiral paracyclophane and chiral 1, 2-cyclohexanediamine, and the chiral compounds containing chiral oxazoline, chiral binaphthyl, chiral spiro, chiral paracyclophane and chiral 1, 2-cyclohexanediamine are introduced into main body, electron or hole transport material molecules. The organic chiral auxiliary functional material is a main material, an electron transport material or a hole transport material based on 1, 2-cyclohexanediamine, and the preparation of a circular polarization organic light emitting diode device with high luminous efficiency and high luminous asymmetry factor is realized by using the organic chiral auxiliary functional material.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials. More specifically, it relates to functional materials with chiral oxazoline, chiral binaphthalene, chiral spirocycle, chiral p - cyclophane, and chiral 1,2 - cyclohexanediamine as chiral building units, which can be used as host materials, electron - transporting materials, or hole - transporting materials in circularly polarized organic light - emitting diodes. Background Art

[0002] Since Meijer et al. first achieved the preparation of circularly polarized organic light - emitting diodes (CP - OLEDs) in 1997, extensive research has been carried out on the development of CP - OLEDs. Due to the ability of circularly polarized luminescence based on OLEDs to directly generate circularly polarized light efficiently, and its broad application prospects in fields such as 3D displays, self - rotating information communication, and optoelectronic information storage, it has attracted much attention.

[0003] Currently, the research on CP - OLEDs mainly focuses on the construction of chiral luminescent materials in the light - emitting layer, and there is relatively little research on the systematic chiral preparation of functional layers in the device. Therefore, constructing organic chiral auxiliary functional materials to study the chiral luminescence mechanism of organic chiral auxiliary functional layers in the device is of great significance for preparing circularly polarized organic light - emitting diodes with high luminescence asymmetry factors and high luminescence efficiencies. Summary of the Invention

[0004] The technical problem to be solved by the present invention is to provide a series of organic chiral auxiliary functional materials. At the same time, studying the circularly polarized luminescence properties of this series of materials in circularly polarized luminescence devices is of great significance for exploring and obtaining highly efficient circularly polarized luminescence devices.

[0005] Another object of the present invention is to use the constructed organic chiral auxiliary functional materials as host materials, electron - transporting materials, or hole - transporting materials in circularly polarized organic light - emitting diodes to obtain circularly polarized organic electroluminescent devices with high luminescence asymmetry factors and high luminescence efficiencies.

[0006] To achieve the above - mentioned technical objectives, the present invention provides a series of organic chiral host materials, organic chiral electron - transporting materials, and chiral hole - transporting materials, whose structural general formulas are shown as Formulas I, II, III, IV, V, VI, VII, VIII, IX, X, and XI:

[0007]

[0008] Organic Chiral Auxiliary Functional Material I:

[0009] Wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; X 1 、X 2 and X 3is any one of carbon or nitrogen;

[0010] R 1 、R 2 、R 3 、R 4 and R 5 each independently represents any one of hydrogen, halogen-substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl and heteroaryl, and substituted or unsubstituted C10-C30 fused ring group.

[0011] Furthermore, the structural formula of the above-mentioned organic chiral auxiliary functional material I is any one of the following structural formulas:

[0012] Organic chiral auxiliary functional material II:

[0013] wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; Ar 1 is any one of substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3- to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, and substituted or unsubstituted C10-C30 fused ring group;

[0014] Ar and Ar 2 represent any one of hydrogen, substituted or unsubstituted C6-C30 aryl and heteroaryl, and substituted or unsubstituted C10-C30 fused ring group.

[0015] Furthermore, the structural formula of the above-mentioned organic chiral auxiliary functional material II is any one of the following structural formulas:

[0016]

[0017] Organic chiral auxiliary functional material III:

[0018] wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; Ar 1 is any one of substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3- to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, and substituted or unsubstituted C10-C30 fused ring group;

[0019] Ar 2 represents any one of hydrogen, substituted or unsubstituted C6-C30 aryl and heteroaryl, and substituted or unsubstituted C10-C30 fused ring group;

[0020] Ar 3 and Ar 4is any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, or a substituted or unsubstituted C10-C30 fused ring group.

[0021] Furthermore, the structural formula of the above-mentioned organic chiral auxiliary function III is any one of the following structural formulas:

[0022]

[0023] Organic chiral auxiliary functional materials IV and V:

[0024] Among them, R or S indicates that the chiral molecule is dextrorotatory or levorotatory; Ar 1 is any one of hydrogen, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted 3- to 30-membered heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, or a substituted or unsubstituted C10-C30 fused ring group;

[0025] R, Ar, and Ar 2 represent any one of hydrogen, a substituted or unsubstituted C6-C30 aryl group and heteroaryl group, or a substituted or unsubstituted C10-C30 fused ring group;

[0026] Furthermore, the structural formulas of the above-mentioned organic chiral auxiliary functional materials IV and V are any one of the following structural formulas:

[0027]

[0028] Organic chiral auxiliary functional materials VI and VII:

[0029] Among them, R or S indicates that the chiral molecule is dextrorotatory or levorotatory; Ar 1 is any one of hydrogen, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted 3- to 30-membered heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, or a substituted or unsubstituted C10-C30 fused ring group;

[0030] R, Ar, and Ar 2 represent any one of hydrogen, a substituted or unsubstituted C6-C30 aryl group and heteroaryl group, or a substituted or unsubstituted C10-C30 fused ring group;

[0031] Ar 3 and Ar 4is any one of a substituted or unsubstituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, and a substituted or unsubstituted C10-C30 fused ring group.

[0032] Furthermore, the structural formulas of the above-mentioned organic chiral auxiliary functional materials VI and VII are any one of the following structural formulas:

[0033]

[0034] Organic chiral auxiliary functional materials VIII and IX:

[0035] Among them, R or S represents that the chiral molecule is dextrorotatory or levorotatory; Ar, Ar 2 and Ar 3 is any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, and a substituted or unsubstituted C10-C30 fused ring group;

[0036] Furthermore, the structural formulas of the above-mentioned organic chiral auxiliary functional materials VIII and IX are any one of the following structural formulas:

[0037]

[0038] Organic chiral auxiliary functional material X:

[0039] R or S represents that the chiral molecule is dextrorotatory or levorotatory; Ar is any one of a substituted or unsubstituted C3-C30 alkyl group and a cycloalkyl group; Py is any one of a substituted or unsubstituted azaaryl group.

[0040] Furthermore, the structural formula of the above-mentioned organic chiral auxiliary function X is any one of the following structural formulas:

[0041]

[0042] Organic chiral auxiliary functional material XI:

[0043] Among them, R or S represents that the chiral molecule is dextrorotatory or levorotatory; X is any one of C, N, O, and S;

[0044] Ar is any one of a substituted or unsubstituted C3-C30 alkyl group and a cycloalkyl group; Py is any one of a substituted or unsubstituted azaaryl group;

[0045] Ar 1 and Ar 2 represent a substituted or unsubstituted C6-C30 aryl group and any one of a substituted or unsubstituted C10-C30 fused ring group.

[0046] Furthermore, the structural formula of the above-mentioned organic chiral auxiliary functional material XI is any one of the following structural formulas:

[0047]

[0048]

[0049]

[0050] The present invention also provides a preparation method of the above-mentioned organic chiral auxiliary functional material, including:

[0051] Preparation of organic chiral auxiliary functional material I

[0052] Dissolve raw material A, raw material B and triethylamine in dichloromethane, stir evenly, heat up to reflux to obtain intermediate M1; alternatively, dissolve raw material B and triethylamine in dichloromethane, slowly add the dichloromethane solution of raw material A, stir evenly, heat up to reflux and stir the mixture for 12 hours to obtain intermediate M1;

[0053] Remove dichloromethane and excessive triethylamine by rotary evaporation, and dissolve intermediate M1, p-toluenesulfonyl chloride and triethylamine in dichloromethane and stir evenly. Stir overnight at room temperature and then heat up to reflux to obtain material I;

[0054] Furthermore, the synthetic route of the above-mentioned organic chiral auxiliary functional material I is:

[0055]

[0056] Wherein, X 1 、X 2 、X 3 、R 1 、R 2 、R 3 、R 4 and R 5 are defined as in Chemical Formula 1 above.

[0057] Even further, in the present invention, the specific steps of the organic chiral auxiliary functional material I include the following:

[0058] Dissolve raw material A (1.0 equiv) in dichloromethane solvent, and slowly drop it into the dichloromethane mixed solution of raw material B (3.5 equiv) and triethylamine (7.5 equiv) under an ice-water bath. Stir evenly, heat up to reflux for 4 hours. After the solution cools to room temperature, remove the solvent using a rotary evaporator to obtain a solid organic substance. Completely dissolve the solid organic substance with a small amount of dichloromethane, and then slowly drop it into a petroleum ether solution. Stir evenly, precipitate will form. Filter the solid, and wash it with anhydrous ethanol and petroleum ether to obtain intermediate M1.

[0059] The intermediate M1, p-toluenesulfonyl chloride (7.5 equiv), and triethylamine (15 equiv) were added to dichloromethane solvent, stirred evenly, and stirred overnight at room temperature. Then the temperature was raised to reflux for 18 hours. After the solution was cooled to room temperature, it was extracted with an ethyl acetate-water mixed solution to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate was performed to obtain the chiral electron transport material I.

[0060] Preparation of the organic chiral auxiliary functional material II

[0061] The precursor M2 was dissolved in a mixed solvent of hydrogen peroxide and dichloromethane, stirred evenly, and stirred overnight at room temperature to obtain the organic chiral auxiliary functional material II;

[0062] Furthermore, the synthetic route of the above-mentioned organic chiral auxiliary function II is as follows:

[0063]

[0064] Among them, Ar, Ar 1 and Ar 2 are defined as in Chemical Formula 1 above.

[0065] Even further, in the present invention, the specific steps for the organic chiral auxiliary functional material II are as follows:

[0066] The precursor M2 (1.0 equiv) was dissolved in a mixed solvent of hydrogen peroxide (30%, 6 equiv) and dichloromethane, stirred evenly, and stirred overnight at room temperature. After the reaction was complete, it was extracted with a dichloromethane-water mixed solution to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate was performed to obtain the organic chiral auxiliary functional material II.

[0067] Preparation of the organic chiral auxiliary functional material III

[0068] When Ar 3 and Ar 4 are the same, the precursor M3 and the raw material C were dissolved in 1,4-dioxane, the gas was exchanged 3 times, and then tetrakis(triphenylphosphine)palladium and potassium carbonate were added under nitrogen protection, stirred evenly, and the temperature was raised to reflux to obtain the material III;

[0069] When Ar 3 and Ar 4At different times, precursor M3 and raw material C are dissolved in 1,4-dioxane. The air is replaced three times, and then palladium tetrakis(triphenylphosphine) and potassium carbonate are added under nitrogen protection. After stirring evenly, the temperature is raised to reflux to obtain intermediate M4. Subsequently, intermediate M4 and raw material D are dissolved in 1,4-dioxane. The air is replaced three times, and then palladium tetrakis(triphenylphosphine) and potassium carbonate are added under nitrogen protection. After stirring evenly, the temperature is raised to reflux to obtain Material III.

[0070] Furthermore, the synthesis route of the above-mentioned organic chiral auxiliary functional material III is as follows:

[0071]

[0072] Ar, Ar 1 、Ar 2 、Ar 3 and Ar 4 as defined in Chemical Formula 3 or 4 above.

[0073] Even further, in the present invention, the organic chiral auxiliary functional material III includes the following steps:

[0074] When Ar 3 and Ar 4 are the same, after adding precursor M3 (1.0 equiv), raw material C (4.5 equiv) and anhydrous 1,4-dioxane to the reactor, the air is fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (9.0 equiv) and palladium tetrakis(triphenylphosphine) (0.02 equiv) are added to the system. The mixture is stirred, the temperature is raised to reflux, and the reflux reaction is carried out for 24 hours. After the solution is cooled to room temperature, it is extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is carried out to obtain the organic chiral auxiliary functional material III;

[0075] When Ar 3 and Ar 4At different times, the precursor M3 (1.0 equiv), the raw material C (2.5 equiv) and anhydrous 1,4-dioxane were added to the reactor, stirred evenly, and the air was fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (5.0 equiv) and tetrakistriphenylphosphine palladium (0.01 equiv) were added to the system, and the mixture was stirred and heated to reflux. The reaction was refluxed for 24 hours. After the solution was cooled to room temperature, it was extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and petroleum ether-ethyl acetate column chromatography was performed to obtain the intermediate M4. Subsequently, the intermediate M4 (1.0 equiv), the raw material D (2.5 equiv) and anhydrous 1,4-dioxane were added to the reactor, stirred evenly, and the air was fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (5.0 equiv) and tetrakistriphenylphosphine palladium (0.01 equiv) were added to the system, the mixture was stirred, and the temperature was raised to reflux. The reflux reaction was carried out for 24 hours. After the solution was cooled to room temperature, it was extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and petroleum ether-ethyl acetate column chromatography was performed to obtain an organic chiral auxiliary functional material III.

[0076] Preparation of organic chiral auxiliary functional materials IV and V

[0077] Dissolve the precursor M5 or M6 in a mixed solvent of hydrogen peroxide and dichloromethane, stir evenly, and stir at room temperature overnight to obtain the organic chiral auxiliary functional material IV or V;

[0078] Furthermore, the synthesis route of the organic chiral auxiliary functional material IV or V is:

[0079]

[0080] Among them, R, Ar, Ar 1 and Ar 2 As defined in Chemical Formula 5 or 6 above.

[0081] Furthermore, in the present invention, the organic chiral auxiliary functional materials IV and V include the following steps:

[0082] The precursor M5 or M6 (1.0 equiv) was dissolved in a mixed solvent of hydrogen peroxide (30%, 6 equiv) and dichloromethane, stirred evenly, and stirred at room temperature overnight. After the reaction was complete, the mixture was extracted with a dichloromethane-water mixed solution to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and petroleum ether-ethyl acetate column chromatography was performed to obtain an organic chiral auxiliary functional material IV or V.

[0083] Preparation of organic chiral auxiliary functional materials VI and VII

[0084] When Ar 3 and Ar 4 are the same, the precursor M7 or M8 and the raw material C are dissolved in 1,4 - dioxane, the gas is exchanged three times, and then tetrakis(triphenylphosphine)palladium and potassium carbonate are added under nitrogen protection, stirred evenly, and heated to reflux to obtain the material VI or VII;

[0085] When Ar 3 and Ar 4 are different, the precursor M7 or M8 and the raw material C are dissolved in 1,4 - dioxane, the gas is exchanged three times, and then tetrakis(triphenylphosphine)palladium and potassium carbonate are added under nitrogen protection, stirred evenly, and heated to reflux to obtain the intermediate M9 or M10; Subsequently, the intermediate M9 or M10 and the raw material D are dissolved in 1,4 - dioxane, the gas is exchanged three times, and then tetrakis(triphenylphosphine)palladium and potassium carbonate are added under nitrogen protection, stirred evenly, and heated to reflux to obtain the material III;

[0086] Furthermore, the synthetic routes of the above - mentioned organic chiral auxiliary functional materials VI and VII are as follows:

[0087]

[0088] Among them, Ar, Ar 1 、Ar 2 、Ar 3 and Ar 4 are defined as in the above chemical formulas 7, 8, 9 and 10.

[0089] Even further, in the present invention, the preparation of the organic chiral auxiliary functional materials VI and VII includes the following steps:

[0090] When Ar 3 and Ar 4 are the same, after adding the precursor M7 or M8 (1.0 equiv), the raw material C (4.5 equiv) and anhydrous 1,4 - dioxane into the reactor, the air is fully displaced with nitrogen three times, and then dry potassium carbonate (9.0 equiv) and tetrakis(triphenylphosphine)palladium (0.02 equiv) are added to the system, the mixture is stirred, heated to reflux, and reflux - reacted for 24 hours. After the solution is cooled to room temperature, it is extracted with an ethyl acetate - water mixed solvent to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether - ethyl acetate is carried out to obtain the organic chiral auxiliary functional material VI or VII;

[0091] When Ar 3 and Ar 4At different times, after adding precursor M7 or M8 (1.0 equiv), raw material C (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, stir evenly, displace air with nitrogen three times fully, then add dry potassium carbonate (5.0 equiv) and palladium tetrakistriphenylphosphine (0.01 equiv) to the system, stir the mixture, heat up to reflux, and carry out the reflux reaction for 24 hours. After the solution is cooled to room temperature, extract with an ethyl acetate-water mixed solvent to obtain an organic phase. This organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is carried out to obtain intermediate M9 or M10. Subsequently, after adding intermediate M9 or M10 (1.0 equiv), raw material D (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, stir evenly, displace air with nitrogen three times fully, then add dry potassium carbonate (5.0 equiv) and palladium tetrakistriphenylphosphine (0.01 equiv) to the system, stir the mixture, heat up to reflux, and carry out the reflux reaction for 24 hours. After the solution is cooled to room temperature, extract with an ethyl acetate-water mixed solvent to obtain an organic phase. This organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is carried out to obtain organic chiral auxiliary functional material VI or VII.

[0092] Preparation of Organic Chiral Auxiliary Functional Material VIII

[0093] Dissolve precursor M11 in a mixed solvent of hydrogen peroxide and dichloromethane, stir evenly, and stir at room temperature overnight to obtain organic chiral auxiliary functional material VIII;

[0094] Furthermore, the synthetic route of the above chiral electron transport material VIII is as follows:

[0095]

[0096] Among them, Ar is defined as in the above chemical formula 11.

[0097] Even further, in the present invention, the preparation of organic chiral auxiliary functional material VIII includes the following steps:

[0098] Dissolve precursor M11 (1.0 equiv) in a mixed solvent of hydrogen peroxide (30%, 6 equiv) and dichloromethane, stir evenly, stir at room temperature overnight. After the reaction is complete, extract with a dichloromethane-water mixed solution to obtain an organic phase. This organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is carried out to obtain organic chiral auxiliary functional material VIII.

[0099] Preparation of Organic Chiral Auxiliary Functional Material IX

[0100] When Ar3 and Ar 4 When they are the same, dissolve the precursor M12 and the raw material C in 1,4 - dioxane, change the gas three times, then add palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain Material IX;

[0101] When Ar 3 and Ar 4 are different, dissolve the precursor M12 and the raw material C in 1,4 - dioxane, change the gas three times, then add palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain Intermediate M13; Subsequently, dissolve Intermediate M12 and raw material D in 1,4 - dioxane, change the gas three times, then add palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain Material IX;

[0102] Furthermore, the synthetic route of the above - mentioned organic chiral auxiliary functional material IX is as follows:

[0103]

[0104] wherein, Ar, Ar 2 and Ar are defined as in Chemical Formulas 12 and 13 above.

[0105] Even further, in the present invention, the preparation of the organic chiral auxiliary functional material IX includes the following steps:

[0106] When Ar 3 and Ar 4 are the same, after adding the precursor M12 (1.0 equiv), the raw material C (4.5 equiv) and anhydrous 1,4 - dioxane into the reactor, displace the air with nitrogen three times fully, then add dry potassium carbonate (9.0 equiv) and palladium tetrakis(triphenylphosphine) (0.02 equiv) to the system, stir the mixture, heat up to reflux, and carry out the reflux reaction for 24 hours. After the solution is cooled to room temperature, extract it with an ethyl acetate - water mixed solvent to obtain an organic phase. This organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether - ethyl acetate is carried out to obtain the organic chiral auxiliary functional material IX;

[0107] When Ar 3 and Ar 4At different times, after adding precursor M12 (1.0 equiv), raw material C (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, stir evenly, displace air with nitrogen three times fully, then add dry potassium carbonate (5.0 equiv) and tetrakis(triphenylphosphine)palladium (0.01 equiv) into the system, stir the mixture, heat up to reflux, and carry out reflux reaction for 24 hours. After the solution is cooled to room temperature, extract with an ethyl acetate-water mixed solvent to obtain an organic phase. This organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is carried out to obtain intermediate M13. Subsequently, after adding intermediate M13 (1.0 equiv), raw material D (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, stir evenly, displace air with nitrogen three times fully, then add dry potassium carbonate (5.0 equiv) and tetrakis(triphenylphosphine)palladium (0.01 equiv) into the system, stir the mixture, heat up to reflux, and carry out reflux reaction for 24 hours. After the solution is cooled to room temperature, extract with an ethyl acetate-water mixed solvent to obtain an organic phase. This organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is carried out to obtain the organic chiral auxiliary functional material IX.

[0108] Preparation of Organic Chiral Auxiliary Functional Material X

[0109] Dissolve precursor M14 and raw material C in 1,4-dioxane, change the gas three times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, and heat up to reflux to obtain intermediate M15; dissolve intermediate M15 and raw material E in 1,4-dioxane, change the gas three times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, and heat up to reflux to obtain intermediate M16; the dosage ratio of the precursor M15, raw material E, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; dissolve intermediate M16 and raw material F in a mixed solvent of toluene, ethanol and water, change the gas three times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, and heat up to reflux to obtain material X; the dosage ratio of the intermediate M16, raw material F, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5;

[0110] Furthermore, the synthetic route of the above-mentioned organic chiral auxiliary functional material X is as follows:

[0111]

[0112] Among them, Ar, Ar 2 and Py are defined as in the above chemical formula 14.

[0113] Furthermore, in the present invention, the organic chiral auxiliary functional material X specifically includes the following steps:

[0114] After adding the precursor M14 (1.0 equiv), raw material C (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, the air was fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (5.0 equiv) and tetrakis(triphenylphosphine)palladium (0.01 equiv) were added to the system. The mixture was stirred, heated to reflux, and refluxed for 24 hours. After the solution was cooled to room temperature, it was extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate was performed to obtain intermediate M15. After adding intermediate M15 (1.0 equiv), raw material E (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, it was stirred evenly, the air was fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (5.0 equiv) and tetrakis(triphenylphosphine)palladium (0.01 equiv) were added to the system. The mixture was stirred, heated to reflux, and refluxed for 24 hours. After the solution was cooled to room temperature, it was extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate was performed to obtain intermediate M16. Subsequently, after adding intermediate M16 (1.0 equiv), raw material F (2.5 equiv) and toluene / ethanol / water (Vtol: VEtOH: VH2O = 3:1:1) into the reactor, it was stirred evenly, the air was fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (5.0 equiv) and tetrakis(triphenylphosphine)palladium (0.01 equiv) were added to the system. The mixture was stirred, heated to reflux, and refluxed for 24 hours. After the solution was cooled to room temperature, it was extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate was performed to obtain the organic chiral auxiliary functional material X.

[0115] Preparation of Organic Chiral Auxiliary Functional Material XI

[0116] Dissolve the precursor M14 and raw material C in 1,4-dioxane, replace the gas three times, and then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, and heat to reflux to obtain intermediate M15. Subsequently, dissolve intermediate M15 and raw material G in 1,4-dioxane, replace the gas three times, and then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, and heat to reflux to obtain material XI;

[0117] Furthermore, the synthetic route of the above organic chiral auxiliary functional material XI is as follows:

[0118]

[0119] wherein, X, Ar, Ar 1 and Ar 1 are as defined in Chemical Formula 15 above.

[0120] Furthermore, in the present invention, the specific steps for the organic chiral auxiliary functional material XI include the following:

[0121] After adding the precursor M14 (1.0 equiv), the raw material C (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, the air is fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (5.0 equiv) and tetrakis(triphenylphosphine)palladium (0.01 equiv) are added to the system. The mixture is stirred, heated to reflux, and refluxed for 24 hours. After the solution is cooled to room temperature, it is extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is performed to obtain the intermediate M15; after adding the intermediate M15 (1.0 equiv), the raw material G (2.5 equiv) and anhydrous 1,4-dioxane into the reactor, it is stirred evenly, the air is fully replaced with nitrogen three times. Subsequently, dry potassium carbonate (5.0 equiv) and tetrakis(triphenylphosphine)palladium (0.01 equiv) are added to the system. The mixture is stirred, heated to reflux, and refluxed for 24 hours. After the solution is cooled to room temperature, it is extracted with an ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether-ethyl acetate is performed to obtain the organic chiral auxiliary functional material XI.

[0122] Another object of the present invention is to provide a circularly polarized organic electroluminescent device, the circularly polarized organic electroluminescent device comprising an organic chiral auxiliary functional material; and to provide an application of the above-mentioned organic chiral auxiliary functional material in the preparation of a circularly polarized electroluminescent device.

[0123] Preferably, the circularly polarized organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer disposed between the second electrodes, wherein the organic layer comprises an auxiliary functional layer, and the auxiliary functional layer comprises the above-mentioned organic chiral auxiliary functional material.

[0124] Preferably, the organic layer further comprises a light-emitting layer, an electron transport layer, and a hole transport layer between the first electrode and the second electrode. The light-emitting layer, the electron transport layer, and the hole transport layer among the above are a chiral host layer, a chiral organic electron transport layer, and a chiral organic hole transport layer in the light-emitting layer, and the chiral host layer, the chiral organic electron transport layer, and the chiral organic hole transport layer in the light-emitting layer comprise the above-mentioned organic chiral auxiliary functional material.

[0125] Further, the chiral organic layer includes one or more of a chiral host material, a chiral organic electron transport layer, and a chiral organic hole transport layer. However, the structure is not limited thereto.

[0126] In the present invention, the preparation method of the circularly polarized organic electroluminescent device is not limited. Preferably, metals, conductive oxides, and their alloys are evaporated on a substrate by methods such as thin film evaporation, electron beam evaporation, or physical vapor deposition to form an anode, and then an organic layer is formed thereon and a cathode is evaporated to finally obtain a circularly polarized organic electroluminescent device.

[0127] Further, the above-mentioned chiral organic layer includes a chiral host layer, a chiral organic electron transport layer, and a chiral hole transport layer in the light-emitting layer, and these layer structures are evaporated by the above methods such as thin film evaporation, electron beam evaporation, or physical vapor deposition, or a solvent method can be used to replace the evaporation method, such as spin coating, blade coating, and screen printing. Detailed implementation mode

[0128] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative efforts belong to the scope of protection of the present invention.

[0129] Embodiment 1

[0130] Organic chiral functional auxiliary material (R)-I-01:

[0131]

[0132] (R)-I-01 corresponds to a specific example of (R / S)-I-C in claim 2;

[0133] Among them, R means that the chiral molecule is a dextrorotatory body, R 1 , R 2 and R 3 are hydrogen, R 4 is ethyl, and R 5 is hydrogen;

[0134] The preparation method is:

[0135]

[0136] Dissolve raw material A-001 (2.6 g, 10 mmol) in 40 mL of dichloromethane solvent. Slowly add it dropwise to a 20 mL dichloromethane mixed solution of raw material B-001 (3.1 g, 35 mmol) and triethylamine (7.5 g, 75 mmol) under an ice-water bath. Stir evenly, heat to reflux for 4 hours. After the solution cools to room temperature, remove the solvent using a rotary evaporator to obtain a solid organic substance. Dissolve the solid organic substance completely with a small amount of dichloromethane, and then slowly add it dropwise to a petroleum ether solution. Stir evenly, precipitate will form. Filter the solid, wash it with 100 mL of anhydrous ethanol and 100 mL of petroleum ether to obtain intermediate M1 (3.8 g).

[0137] Add intermediate (R)-M-01, p-toluenesulfonyl chloride (14 g, 75 mmol) and triethylamine (15 g, 150 mmol) to 40 mL of dichloromethane solvent. Stir evenly and stir at room temperature overnight. Heat to reflux for 18 hours. After the solution cools to room temperature, extract it three times with an equal-volume ethyl acetate-water mixed solution to obtain organic phase A. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography is carried out with petroleum ether:ethyl acetate = 2:1 to obtain the organic chiral functional auxiliary material (R)-I-01 (2.7 g, yield: 73%).

[0138] The obtained compound (R)-I-01 was detected and analyzed, and the results are as follows:

[0139] Mass spectrometry test: Theoretical value: 369.21; Test value: 369.47.

[0140] Example 2

[0141] Organic chiral functional auxiliary material (R)-II-17:

[0142]

[0143] (R)-II-17 corresponds to a specific example of (R / S)-II-B in claim 5;

[0144] Among them, R is the dextrorotatory body of this chiral molecule, Ar 2 is hydrogen, and Ar is phenyl;

[0145] The preparation method is as follows:

[0146]

[0147] Dissolve the precursor (R)-M2-17 (1.2 g, 2 mmol) in a mixed solvent of hydrogen peroxide (30%, 18 mmol) and 10 mL of dichloromethane, stir evenly, stir overnight at room temperature, extract three times with an equal volume of dichloromethane-water mixed solution to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography is performed with petroleum ether:ethyl acetate = 10:1 to obtain the organic chiral auxiliary functional material (R)-II-17 (0.98 g, yield: 75%).

[0148] The obtained compound (R)-II-17 was tested and analyzed, and the results are as follows:

[0149] Mass spectrometry test: Theoretical value: 654.19; Test value: 654.13.

[0150] Example 3

[0151] Organic chiral functional auxiliary material (R)-III-01:

[0152]

[0153] (R)-III-01 corresponds to a specific example of (R / S)-III-A in claim 5;

[0154] Among them, R is the dextrorotatory form of this chiral molecule, Ar 2 is hydrogen, Ar 3 and Ar 4 are both phenyl groups;

[0155] The preparation method is as follows:

[0156]

[0157] After adding the precursor (R)-M3-01 (1.4 g, 5 mmol), the raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane to the reactor, replace the air with nitrogen three times. Under nitrogen protection, add dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) to the system, stir evenly, heat to reflux for 24 hours. After the solution is cooled to room temperature, extract with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography is performed with petroleum ether:ethyl acetate = 20:1 to obtain the organic chiral auxiliary functional material (R)-III-01 (1.91 g, yield: 65%).

[0158] The obtained compound (R)-III-01 was tested and analyzed, and the results are as follows:

[0159] Mass spectrometry test: Theoretical value: 588.26; Test value: 588.13.

[0160] Example 4

[0161] Organic chiral functional auxiliary material (S)-III-36:

[0162]

[0163] (S)-III-36 corresponds to a specific example of (R / S)-III-B in Claim 5;

[0164] wherein, S is the levorotatory form of the chiral molecule, Ar 2 is hydrogen, Ar 3 is phenyl, Ar 4 is p-tolyl;

[0165] The preparation method is as follows:

[0166]

[0167] After adding the precursor (S)-M3-36 (1.4 g, 5 mmol), raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system, stirred evenly, heated to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was carried out with petroleum ether:ethyl acetate = 8:1 to obtain the intermediate (S)-M4-36 (1.75 g, yield: 76%).

[0168] After adding the intermediate (S)-M4-36, raw material D-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system, stirred evenly, heated to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was carried out with petroleum ether:ethyl acetate = 20:1 to obtain the organic chiral auxiliary functional material (S)-III-36 (1.65 g, yield: 53%).

[0169] The obtained compound (S)-III-36 was detected and analyzed, and the results are as follows:

[0170] Mass spectrometry test: Theoretical value: 624.87; Test value: 624.79.

[0171] Example 5

[0172] Organic chiral functional auxiliary material (R)-IV-14:

[0173]

[0174] (R)-IV-14 corresponds to the specific example of (R / S)-IV-B in Claim 9;

[0175] Among them, R is the dextrorotatory form of this chiral molecule, Ar is tert-butyl, and R is hydrogen;

[0176] The preparation method is as follows:

[0177]

[0178] Dissolve the precursor (R)-M5-14 (1.0 g, 2 mmol) in a mixed solvent of hydrogen peroxide (30%, 18 mmol) and 10 mL of dichloromethane, stir evenly, stir overnight at room temperature, extract three times with an equal volume of dichloromethane-water mixed solution to obtain the organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography is carried out with petroleum ether: ethyl acetate = 10:1 to obtain the organic chiral auxiliary functional material (R)-IV-14 (0.81 g, yield: 75%).

[0179] The obtained compound (R)-IV-14 was detected and analyzed, and the results are as follows:

[0180] Mass spectrometry test: Theoretical value: 540.71; Test value: 540.65.

[0181] Example 6

[0182] Organic chiral functional auxiliary material (S)-V-05:

[0183]

[0184] (S)-V-05 corresponds to the specific example of (R / S)-V-A in Claim 9;

[0185] Among them, S is the levorotatory form of this chiral molecule, R is hydrogen, and Ar is phenyl;

[0186] The preparation method is as follows:

[0187]

[0188] Dissolve the precursor (S)-M6-05 (1.3 g, 2 mmol) in a mixed solvent of hydrogen peroxide (30%, 18 mmol) and 10 mL of dichloromethane, stir evenly, stir overnight at room temperature, extract three times with an equal volume of dichloromethane-water mixed solution to obtain the organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether:ethyl acetate = 10:1 is carried out to obtain the organic chiral auxiliary functional material (S)-V-05 (1.08 g, yield: 78%).

[0189] The obtained compound (S)-V-05 was tested and analyzed, and the results are as follows:

[0190] Mass spectrometry test: Theoretical value: 692.73; Test value: 692.65.

[0191] Example 7

[0192] Organic chiral functional auxiliary material (R)-VI-13:

[0193]

[0194] (R)-VI-13 corresponds to a specific example of (R / S)-VI-B in Claim 9;

[0195] Among them, R is the dextrorotatory body of the chiral molecule, R is hydrogen, Ar 1 and Ar 2 is phenyl;

[0196] The preparation method is as follows:

[0197]

[0198] After adding the precursor (R)-M7-13 (1.3 g, 5 mmol), the raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane to the reactor, the air is fully replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) are added to the system, stirred evenly, heated to reflux for 24 hours. After the solution is cooled to room temperature, it is extracted with an equal volume of ethyl acetate-water mixed solvent to obtain the organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography with petroleum ether:ethyl acetate = 15:1 is carried out to obtain the organic chiral auxiliary functional material (R)-VI-13 (1.91 g, yield: 65%).

[0199] The obtained compound (R)-VI-13 was tested and analyzed, and the results are as follows:

[0200] Mass spectrometry test: Theoretical value: 554.27; Test value: 554.23.

[0201] Example 8

[0202] Organic chiral functional auxiliary material (S)-VI-48:

[0203]

[0204] (S)-VI-48 corresponds to a specific example of (R / S)-VI-C in Claim 9;

[0205] wherein S is the levorotatory form of the chiral molecule, R is hydrogen, and Ar 1 is phenyl, and Ar 2 is p-tolyl;

[0206] The preparation method is as follows:

[0207]

[0208] After adding the precursor (S)-M7-48 (1.6 g, 5 mmol), raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air in the reactor was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was performed using petroleum ether:ethyl acetate = 6:1 to obtain the intermediate (S)-M9-48 (1.07 g, yield: 45%).

[0209] After adding the intermediate (S)-M9-48, raw material D-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air in the reactor was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was performed using petroleum ether:ethyl acetate = 30:1 to obtain the organic chiral auxiliary functional material (S)-VI-48 (1.21 g, yield: 37%).

[0210] The obtained compound (S)-VI-48 was detected and analyzed, and the results are as follows:

[0211] Mass spectrometry test: Theoretical value: 654.86; Test value: 654.83.

[0212] Example 9

[0213] Organic chiral functional auxiliary material (R)-VII-01:

[0214]

[0215] (R)-VII-01 corresponds to the specific example of (R / S)-VII-A in Claim 9;

[0216] wherein, R is the dextrorotatory form of the chiral molecule, R is hydrogen, Ar 1 and Ar 2 is phenyl;

[0217] The preparation method is as follows:

[0218]

[0219] After adding the precursor (R)-M8-01 (3.1 g, 5 mmol), raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air in the reactor was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal-volume ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography with petroleum ether:ethyl acetate = 15:1 was carried out to obtain the organic chiral auxiliary functional material (R)-VII-01 (1.16 g, yield: 37%).

[0220] The obtained compound (R)-VII-01 was detected and analyzed, and the results are as follows:

[0221] Mass spectrometry test: Theoretical value: 626.80; Test value: 626.77.

[0222] Example 10

[0223] Organic chiral functional auxiliary material (S)-VII-16:

[0224]

[0225] (S)-VII-16 corresponds to the specific example of (R / S)-VII-A in Claim 9;

[0226] wherein, S is the levorotatory form of the chiral molecule, R is hydrogen, Ar 1 is phenyl, Ar 2 is p-tolyl;

[0227] The preparation method is as follows:

[0228]

[0229] After adding the precursor (S)-M8-16 (1.6 g, 5 mmol), raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal-volume ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was carried out with petroleum ether:ethyl acetate = 6:1 to obtain the intermediate (S)-M10-16 (1.02 g, yield: 45%).

[0230] After adding the intermediate (S)-M9-48, raw material D-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal-volume ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was carried out with petroleum ether:ethyl acetate = 20:1 to obtain the organic chiral auxiliary functional material (S)-VII-16 (1.14 g, yield: 35%).

[0231] The obtained compound (S)-VII-16 was detected and analyzed, and the results are as follows:

[0232] Mass spectrometry test: Theoretical value: 654.85; Test value: 654.83.

[0233] Example 11

[0234] Organic chiral functional auxiliary material (R)-VIII-03:

[0235]

[0236] (R)-VIII-03 corresponds to a specific example of (R / S)-VIII in claim 12;

[0237] Among them, R is the dextrorotatory body of this chiral molecule, and Ar is phenyl;

[0238] The preparation method is as follows:

[0239]

[0240] Dissolve the precursor (R)-M11-03 (1.2 g, 2 mmol) in a mixed solvent of hydrogen peroxide (30%, 18 mmol) and 10 mL of dichloromethane, stir evenly, stir overnight at room temperature, extract three times with an equal-volume dichloromethane-water mixed solution to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography is performed with petroleum ether:ethyl acetate = 10:1 to obtain the organic chiral auxiliary functional material (R)-VIII-03 (0.79 g, yield: 65%).

[0241] The obtained compound (R)-VIII-03 was detected and analyzed, and the results are as follows:

[0242] Mass spectrometry test: Theoretical value: 608.20; Test value: 608.15.

[0243] Example 12

[0244] Organic chiral functional auxiliary material (S)-IX-01:

[0245]

[0246] (S)-IX-01 corresponds to a specific example of (R / S)-IX in claim 12;

[0247] Among them, S is the levorotatory form of this chiral molecule, and Ar is a phenyl group;

[0248] The preparation method is as follows:

[0249]

[0250] After adding the precursor (S)-M12-01 (1.2 g, 5 mmol), raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane to the reactor, replace the air with nitrogen three times. Under nitrogen protection, add dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) to the system, stir evenly, heat up to reflux for 24 hours. After the solution is cooled to room temperature, extract with an equal-volume ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase is dried over anhydrous magnesium sulfate, the solvent is removed using a rotary evaporator, and column chromatography is performed with petroleum ether:ethyl acetate = 15:1 to obtain the organic chiral auxiliary functional material (S)-IX-01 (1.66 g, yield: 61%).

[0251] The obtained compound (S)-IX-01 was detected and analyzed, and the results are as follows:

[0252] Mass spectrometry test: Theoretical value: 544.74; Test value: 544.69.

[0253] Example 13

[0254] Organic chiral functional auxiliary material (R)-X-01:

[0255]

[0256] (R)-X-01 corresponds to the specific example of (R / S)-X-A in Claim 16;

[0257] Among them, R is the dextrorotatory isomer of this chiral molecule, Ar is cyclohexyl, Ar 1 is phenyl, and Py is pyridyl;

[0258] The preparation method is as follows:

[0259]

[0260] After adding the precursor (R)-M14-01 (0.57 g, 5 mmol), raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air in the reactor was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was performed with petroleum ether:ethyl acetate = 5:1 to obtain the intermediate (R)-M15-01 (1.06 g, yield: 80%);

[0261] After adding the intermediate (R)-M15-01, raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air in the reactor was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was performed with petroleum ether:ethyl acetate = 20:1 to obtain the intermediate (R)-M16-01 (1.87 g, yield: 65%);

[0262] After adding the intermediate (R)-M16-01, the raw material C-001 (3.5 g, 22.5 mmol), and a mixed solvent of 40 mL of toluene / ethanol / water (Vtol: VEtOH: VH2O = 3:1:1) into the reactor, the air was thoroughly displaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal-volume ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography on a petroleum ether column was performed to obtain the organic chiral auxiliary functional material (R)-X-01 (1.74 g, yield: 61%).

[0263] The obtained compound (R)-X-01 was tested and analyzed, and the results are as follows:

[0264] Mass spectrometry test: Theoretical value: 572.76; Test value: 572.71.

[0265] Example 14

[0266] Organic chiral functional auxiliary material (R)-XI-01:

[0267]

[0268] (R)-XI-01 corresponds to a specific example of (R / S)-XI-A in Claim 16;

[0269] Among them, R is the dextrorotatory form of this chiral molecule, Ar is cyclohexyl, Ar 1 is phenyl, Ar 2 is phenyl;

[0270] The preparation method is as follows:

[0271]

[0272] After adding the precursor (R)-M14-01 (0.57 g, 5 mmol), the raw material C-001 (3.5 g, 22.5 mmol), and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was thoroughly displaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal-volume ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography with petroleum ether: ethyl acetate = 5:1 was performed to obtain the intermediate (R)-M15-01 (1.06 g, yield: 80%);

[0273] After adding the intermediate (R)-M15-01, the raw material G-001 (3.5 g, 22.5 mmol), and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was thoroughly displaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of a mixed solvent of ethyl acetate and water to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was performed using petroleum ether:ethyl acetate = 10:1 to obtain the organic chiral auxiliary functional material (R)-X-01 (1.88 g, yield: 50%).

[0274] The obtained compound (R)-XI-01 was detected and analyzed, and the results are as follows:

[0275] Mass spectrometry test: Theoretical value: 753.01; Test value: 752.96.

[0276] Example 15

[0277] Organic chiral functional auxiliary material (R)-XI-61:

[0278]

[0279] (R)-XI-61 corresponds to a specific example of (R / S)-XI-B in claim 16;

[0280] Among them, R is the dextrorotatory form of this chiral molecule, Ar is cyclohexyl, Ar 1 is phenyl, Ar 2 is phenyl;

[0281] The preparation method is as follows:

[0282]

[0283] After adding the precursor (R)-M14-01 (0.57 g, 5 mmol), the raw material C-001 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was carried out with petroleum ether:ethyl acetate = 5:1 to obtain the intermediate (R)-M15-01 (1.06 g, yield: 80%);

[0284] After adding the intermediate (R)-M15-01, the raw material G-002 (3.5 g, 22.5 mmol) and 40 mL of anhydrous 1,4-dioxane into the reactor, the air was replaced with nitrogen three times. Under nitrogen protection, dry potassium carbonate (6.2 g, 45 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) were added to the system. After stirring evenly, the temperature was raised to reflux for 24 hours. After the solution was cooled to room temperature, it was extracted with an equal volume of ethyl acetate-water mixed solvent to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and column chromatography was carried out with petroleum ether:ethyl acetate = 15:1 to obtain the organic chiral auxiliary functional material (R)-XI-61 (1.2 g, yield: 50%).

[0285] The obtained compound (R)-XI-61 was detected and analyzed, and the results are as follows:

[0286] Mass spectrometry test: Theoretical value: 748.97; Test value: 748.91.

[0287] Since the structural general formula is Formula I, II, III, IV, V, VI, VII, VIII, IX, X and XI in the present invention, the synthesis routes and principles of other compounds are the same as those of the above-listed examples, so they will not be enumerated here. Among them, in Examples 16-52 of the present invention, the following organic chiral functional auxiliary materials shown in Table 1 can be obtained according to the above preparation method:

[0288] Table 1 Compounds prepared in Examples 16-52:

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297] The circularly polarized organic light-emitting device is prepared by using the organic chiral functional auxiliary material provided in the above embodiment. The circularly polarized organic electroluminescent device includes an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode.

[0298] Among them, the organic chiral auxiliary functional material can be used as the host material in the light-emitting layer, the electron transport material in the electron transport layer, or the hole transport material in the hole transport layer.

[0299] Example 51

[0300] This example provides a method for preparing a circularly polarized organic electroluminescent device by using a chiral electron transport material, which includes the following steps: placing an ITO glass substrate with a coating thickness of 80 nm in distilled water and washing it twice, sonicating for 30 minutes, repeatedly washing it twice with distilled water, sonicating for 10 minutes. After the distilled water washing is completed, sonicating it in solvents such as isopropanol, acetone, and methanol in sequence and then drying it, transferring it to a plasma cleaner, washing the above substrate for 5 minutes, and sending it to an evaporation coater.

[0301] First, on the ITO anode layer, the hole injection layer material MoO3 is evaporated by vacuum evaporation with a thickness of 2 nm; 60 nm of TAPC is vacuum-evaporated as the hole transport layer on the hole injection layer; on the hole transport layer, a light-emitting layer with a thickness of 25 nm of the host material mCP and the light-emitting material Ir(bt)2acac is vacuum-evaporated, where the weight ratio of the host material to the light-emitting material is 9:1; then, on the above light-emitting layer, 40 nm of the (R)-I-01 compound provided in Example 1 is vacuum-evaporated as the chiral auxiliary electron transport layer; on the above chiral auxiliary electron transport layer, 0.7 nm of LiF is vacuum-evaporated as the electron injection layer; finally, 100 nm of Al is vacuum-evaporated as the cathode on the electron injection layer, and thus the circularly polarized organic electroluminescent device can be obtained.

[0302] The structural formulas of the materials in the device other than the chiral electron transport layer are as follows:

[0303]

[0304] Examples 52 - 120:

[0305] Referring to the method of Device Example 51 above, the compounds (R)-I-01 (Example 1), (R)-II-17 (Example 2), (R)-IV-14 (Example 5), (S)-V-05 (Example 6), (R)-VIII-03 (Example 11), (R)-I-06 (Example 16), (S)-I-14 (Example 17), (S)-I-28 (Example 18), (R)-I-49 (Example 19), (R)-I-65 (Example 20), (S)-I-79 (Example 21), (R)-I-99 (Example 22), (S)-II-06 (Example 23), (R)-II-24 (Example 24), (R)-II-40 (Example 25), (R)-II-47 (Example 26), (S)-II-68 (Example 27), (R)-IV-02 (Example 32), (S)-IV-19 (Example 33), (S)-IV-36 (Example 34), (R)-V-11 (Example 35), (S)-VIII-01 (Example 40) were respectively selected as the chiral electron transport layer materials, and the luminescent materials were selected from three phosphorescent complexes (Ir(bt)2acac, Ir(ppy)2acac, FIrpic), three TADF molecules (Ac-CNP, DMAC-BP, DMAC-DPS), and three d-f transition rare earth luminescent complexes (CeTBO 2Et , EuI2-N8, Eu(Tp 2Et )2), and circularly polarized organic light-emitting devices were prepared, which were respectively denoted as Examples 52 - 120.

[0306] The luminous efficiency and electroluminescence asymmetry factor of the circularly polarized organic light-emitting devices obtained in the above Examples 51 - 120 were characterized, and the test results are shown in Table 2 below. Among them, the electroluminescence asymmetry factor is an important parameter for measuring the performance of circularly polarized devices. The + or - in the electroluminescence asymmetry factor indicates that the generated light is right-handed or left-handed light, and the numerical value represents the polarization intensity of the light.

[0307] Table 2 Circularly polarized organic light-emitting devices prepared in Examples 51 - 120

[0308]

[0309]

[0310]

[0311] As can be seen from Table 2, the above Examples 51 - 120 of the present invention show the following technical effects:

[0312] In the chiral material of the present invention, chiral oxazoline-based, chiral binaphthalene-based, and chiral p-cyclophane-based derivative functional materials are used as chiral electron transport materials, showing a relatively high luminescence efficiency (12.8%) and a good electroluminescence asymmetry factor (-5.6×10 -3 ). Among them, chiral oxazoline derivative material I and chiral binaphthalene derivative phosphine oxide material II show good performance as chiral electron transport materials. Therefore, this type of material can be used to realize the performance of circularly polarized luminescence in organic light-emitting diode devices.

[0313] Example 121

[0314] This example provides a method for preparing a circularly polarized organic electroluminescent device using a chiral hole transport material, which includes the following steps: placing an ITO glass substrate with a coating thickness of 80 nm in distilled water for cleaning 2 times, ultrasonic washing for 30 minutes, repeatedly cleaning with distilled water 2 times, ultrasonic washing for 10 minutes. After the distilled water cleaning is completed, ultrasonic washing is carried out in sequence with solvents such as isopropanol, acetone, and methanol and then dried, transferred to a plasma cleaner, washing the above substrate for 5 minutes, and sending it to an evaporation coater.

[0315] First, on the ITO anode layer, the hole injection layer material MoO3 is evaporated by vacuum evaporation, with a thickness of 2 nm; (R)-III-01 with a thickness of 60 nm is vacuum evaporated as a chiral auxiliary hole transport layer on the hole injection layer; then, a host material mCP with a thickness of 25 nm and a luminescent material Ir(bt)2acac are vacuum evaporated as a luminescent layer on the hole transport layer, where the weight ratio of the host material to the luminescent material is 9:1; then, TmPyPB with a thickness of 40 nm is vacuum evaporated as an electron transport layer on the above luminescent layer; LiF with a thickness of 0.7 nm is vacuum evaporated as an electron injection layer on the above electron transport layer; finally, Al with a thickness of 100 nm is vacuum evaporated as a cathode on the electron injection layer, and a circularly polarized organic electroluminescent device can be obtained.

[0316] Structural formula of TmPyPB:

[0317]

[0318] Examples 122 - 187

[0319] Referring to the method of Device Example 51 above, the compounds (R)-III-01 (Example 3), (S)-III-36 (Example 4), (R)-VI-13 (Example 7), (S)-VI-48 (Example 8), (R)-VII-01 (Example 9), (S)-VII-16 (Example 10), (S)-IX-01 (Example 12), (R)-XI-01 (Example 14), (R)-XI-61 (Example 15), (S)-III-06 (Example 28), (R)-III-28 (Example 29), (S)-III-51 (Example 30), (R)-III-63 (Example 31), (S)-VI-07 (Example 36), (S)-VI-28 (Example 37), (S)-VI-34 (Example 38), (R)-VII-03 (Example 39), (R)-IX-06 (Example 41), (S)-XI-26 (Example 45), (R)-XI-76 (Example 46), (S)-XI-91 (Example 47), (R)-XI-106 (Example 48), (S)-XI-121 (Example 49), (R)-XI-136 (Example 50) are respectively selected as the chiral hole transport layer materials, and the luminescent materials are selected from three phosphorescent complexes (Ir(bt)2acac, Ir(ppy)2acac, FIrpic), three TADF molecules (Ac-CNP, DMAC-BP, DMAC-DPS), and three d-f transition rare earth luminescent complexes (CeTBO 2Et , EuI2-N8, Eu(Tp 2Et )2), and circularly polarized organic light-emitting devices are prepared, which are respectively denoted as Examples 122 - 187.

[0320] The luminous efficiency and electroluminescence asymmetry factor of the circularly polarized organic light-emitting devices obtained in the above Examples 121 - 187 are characterized, and the test results are shown in Table 3 below. Among them, the electroluminescence asymmetry factor is an important parameter for measuring the performance of circularly polarized devices. The + or - in the electroluminescence asymmetry factor indicates that the generated light is right-handed or left-handed light, and the value represents the polarization intensity of the light.

[0321] Table 3 Circularly polarized organic light-emitting devices prepared in Examples 121 - 187

[0322]

[0323]

[0324]

[0325] As can be seen from Table 3, the above-described Examples 121-187 of the present invention exhibit the following technical effects:

[0326] In the chiral material of the present invention, chiral binaphthalene-based, chiral spiro, chiral p - cyclophane-based, and chiral 1,2 - cyclohexanediamine-derived functional materials are used as chiral hole transport materials, showing relatively high luminescence efficiency (14.8%) and good electroluminescence asymmetry factor (-3.5×10 - 3 ). Among them, the triarylamine material III derived from chiral binaphthalene and the triarylamine material XI derived from chiral 1,2 - cyclohexanediamine show good performance as chiral hole transport materials. Therefore, this type of material can be used to achieve the performance of circularly polarized luminescence in organic light - emitting diode devices.

[0327] Example 188

[0328] This example provides a method for preparing a circularly polarized organic electroluminescent device using a chiral host material, which includes the following steps: Place an ITO glass substrate with a coating thickness of 80 nm in distilled water and wash it 2 times, ultrasonically wash it for 30 minutes, repeatedly wash it 2 times with distilled water, ultrasonically wash it for 10 minutes. After the distilled water washing is completed, ultrasonically wash it in sequence with solvents such as isopropanol, acetone, and methanol and then dry it. Transfer it to a plasma cleaner, wash the above substrate for 5 minutes, and send it to an evaporation coater.

[0329] First, on the ITO anode layer, deposit a hole injection layer material MoO3 by vacuum evaporation, with a thickness of 2 nm; deposit 60 nm of TAPC as a chiral auxiliary hole transport layer above the hole injection layer; then deposit a host material (R)-IV - 14 with a thickness of 25 nm and a luminescent material Ir(bt)2acac as a light - emitting layer above the hole transport layer, where the weight ratio of the host material to the luminescent material is 9:1; then deposit a TmPyPB with a thickness of 40 nm as an electron transport layer on the above light - emitting layer; deposit a LiF with a thickness of 0.7 nm as an electron injection layer on the above electron transport layer; finally, deposit 100 nm of Al as a cathode on the electron injection layer to obtain a circularly polarized organic electroluminescent device.

[0330] Examples 189 - 226

[0331] Referring to the method of the above-mentioned device Example 188, the compounds (R)-IV-14 (Example 5), (R)-VIII-03 (Example 11), (R)-X-01 (Example 13), (R)-XI-61 (Example 15), (R)-IV-02 (Example 32), (R)-X-18 (Example 42), (R)-X-30 (Example 43), (S)-X-50 (Example 44), (S)-XI-62 (Example 45) were respectively selected as the chiral host materials, and the luminescent materials were selected from three phosphorescent complexes (Ir(bt)2acac, Ir(ppy)2acac, FIrpic), three TADF molecules (Ac-CNP, DMAC-BP, DMAC-DPS), and three d-f transition rare earth luminescent complexes (CeTBO 2Et 、EuI2-N8、Eu(Tp 2Et )2). Circularly polarized organic light-emitting devices were prepared and denoted as Examples 189 - 226 respectively.

[0332] The luminous efficiency and electroluminescence asymmetry factor of the circularly polarized organic light-emitting devices obtained in the above Examples 188 - 226 were characterized, and the test results are shown in Table 4 below. Among them, the electroluminescence asymmetry factor is an important parameter for measuring the performance of circularly polarized devices. The + or - in the electroluminescence asymmetry factor indicates that the generated light is right-handed or left-handed light, and the value represents the polarization intensity of the light.

[0333] Table 4 Circularly polarized organic light-emitting devices prepared in Examples 188 - 226

[0334]

[0335]

[0336] As can be seen from Table 4, the above Examples 128 - 226 of the present invention show the following technical effects:

[0337] In the chiral materials of the present invention, phosphine oxide materials IV derived from chiral spirocycles, phosphine oxide materials VIII derived from chiral p - cyclophanes, and chiral 1,2 - cyclohexanediamine-derived functional materials X and XI are used as chiral host materials, showing relatively high luminous efficiency (14.4%) and good electroluminescence asymmetry factor (-3.3×10 -3 ). Therefore, using such materials as the host materials for light-emitting diode devices can enable the devices to have the performance of circularly polarized luminescence.

[0338] The various embodiments in this specification are described in a progressive manner. Each embodiment focuses on the differences from other embodiments. For the same or similar parts among the various embodiments, reference can be made to each other. For the devices disclosed in the embodiments, since they correspond to the methods disclosed in the embodiments, the description is relatively simple. For related parts, reference can be made to the description in the method section.

[0339] The above description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be obvious to those skilled in the art. The general principles defined herein can be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to these embodiments shown herein, but rather will be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. An organic chiral auxiliary functional material, characterized in that, The structural general formula of the organic chiral auxiliary functional material is shown as follows: wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; X 1 , X 2 and X 3 are carbon or nitrogen; R 1 , R 2 , R 3 , R 4 and R 5 each independently selected from any one of hydrogen, halogen-substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl and heteroaryl, and substituted or unsubstituted C10-C30 fused ring group.

2. The organic chiral auxiliary functional material according to claim 1, wherein The organic chiral auxiliary functional material has the following structure:

3. The preparation method of the organic chiral auxiliary functional material I according to claim 1, characterized in that, The method includes: dissolving raw material A, raw material B and triethylamine in dichloromethane, stirring evenly, heating to reflux to obtain intermediate M1; dissolving intermediate M1, p-toluenesulfonyl chloride and triethylamine in dichloromethane, stirring evenly, heating to reflux to obtain material I; The synthetic route is shown as follows:

4. An organic chiral auxiliary functional material, characterized in that of the organic chiral auxiliary functional material The structural general formula is shown as follows: wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; Ar 1 is any one of a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, and a substituted or unsubstituted C10-C30 fused ring group; Ar and Ar 2 Any one selected from hydrogen, substituted or unsubstituted C6-C30 aryl and heteroaryl, and substituted or unsubstituted C10-C30 fused ring group; Ar 3 and Ar 4 is any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, and a substituted or unsubstituted C10-C30 fused ring group.

5. The organic chiral auxiliary functional material according to claim 4, wherein has the following structure:

6. The preparation method of the organic chiral auxiliary functional material II according to claim 4, characterized in that, The method includes: dissolving precursor M2 in hydrogen peroxide and dichloromethane, stirring evenly, reacting at room temperature to obtain material II; The synthetic route is shown as follows:

7. The preparation method of the organic chiral auxiliary functional material III according to claim 4, characterized in that, The preparation method includes: when Ar 3 and Ar 4 are the same, dissolve the precursor M3 and the raw material C in 1,4-dioxane, change the gas three times, then add palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain Material III; the dosage ratio of the precursor M3, the raw material C, palladium tetrakis(triphenylphosphine) and potassium carbonate is: 1:4.5:0.02:9; The synthetic route is shown as follows: When Ar 3 and Ar 4 are different, dissolve the precursor M3 and the raw material C in 1,4-dioxane, change the gas three times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, and heat to reflux to obtain the intermediate M4; the dosage ratio of the precursor M3, the raw material C, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; Subsequently, dissolve the intermediate M4 and the raw material D in 1,4-dioxane, change the gas three times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, and heat to reflux to obtain the material III; the dosage ratio of the intermediate M4, the raw material D, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; The synthetic route is shown as follows:

8. An organic chiral auxiliary functional material, characterized in that, The structural general formula of the organic chiral auxiliary functional material is shown as formulas (R / S)-IV, (R / S)-V, (R / S)-VI and (R / S)-VII: wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; Ar 1 is any one of hydrogen, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, and a substituted or unsubstituted C10-C30 fused ring group; R, Ar, and Ar 2 any one selected from hydrogen, substituted or unsubstituted C6-C30 aryl and heteroaryl, and substituted or unsubstituted C10-C30 fused ring group; Ar 3 and Ar 4 is any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, and a substituted or unsubstituted C10-C30 fused ring group.

9. The organic chiral auxiliary functional material according to claim 8, characterized in that, has the following structure:

10. The preparation method of the organic chiral auxiliary functional materials IV and V according to claim 8, characterized in that, including: Dissolving precursor M5 or M6 in hydrogen peroxide and dichloromethane, stirring evenly, reacting at room temperature to obtain material IV or V; The synthetic route is shown as follows:

11. The preparation method of the organic chiral auxiliary functional materials VI and VII according to claim 8, characterized in that, The preparation method includes: when Ar 3 and Ar 4 are the same, dissolve precursor M7 or M8 and raw material C in 1,4-dioxane, change the gas three times, then add palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain material VI or VII; the dosage ratio of the precursor M7 or M8, raw material C, palladium tetrakis(triphenylphosphine) and potassium carbonate is: 1:4.5:0.02:9; The synthetic route is shown as follows: When Ar 3 and Ar 4 are different, dissolve the precursor M7 or M8 and the raw material C in 1,4-dioxane, replace the air 3 times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain the intermediate M9 or M10; the dosage ratio of the precursor M7 or M8, the raw material C, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; Subsequently, dissolve the intermediate M9 or M10 and the raw material D in 1,4-dioxane, replace the air 3 times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain the material VI or VII; the dosage ratio of the intermediate M9 or M10, the raw material D, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; The synthetic route is shown as follows:

12. An organic chiral auxiliary functional material, characterized in that, The structural general formula of the organic chiral auxiliary functional material is shown as formulas VIII and IX: wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; Ar, Ar 2 and Ar 3 is any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 heteroaryl group, and a substituted or unsubstituted C10-C30 fused ring group.

13. The preparation method of the organic chiral auxiliary functional material VIII according to claim 12, characterized in that, The method includes: dissolving precursor M11 in hydrogen peroxide and dichloromethane, stirring evenly, reacting at room temperature to obtain material VIII; The synthetic route is shown as follows:

14. The preparation method of the organic chiral auxiliary functional material IX according to claim 12, characterized in that, The preparation method includes: when Ar 2 and Ar 3 are the same, dissolve the precursor M12 and the raw material C in 1,4-dioxane, change the gas three times, then add palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stir evenly, heat to reflux to obtain Material IX; the dosage ratio of the precursor M12, the raw material C, palladium tetrakis(triphenylphosphine) and potassium carbonate is: 1:4.5:0.02:9; The synthetic route is shown as follows: When Ar 2 and Ar 3 are different, dissolve the precursor M12 and the raw material C in 1,4-dioxane, replace the air 3 times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain the intermediate M13; the dosage ratio of the precursor M12, the raw material C, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; Subsequently, dissolve the intermediate M13 and the raw material D in 1,4-dioxane, replace the air 3 times, then add tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stir evenly, heat up to reflux to obtain the material IX; the dosage ratio of the intermediate M13, the raw material D, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; The synthetic route is shown as follows:

15. An organic chiral auxiliary functional material, characterized in that, The structural general formula of the organic chiral auxiliary functional material is shown as formulas X and XI: wherein, R or S represents that the chiral molecule is dextrorotatory or levorotatory; X is any one of C, N, O, S; Ar is any one of a substituted or unsubstituted C3-C30 alkyl group or cycloalkyl group; Py is any one of a substituted or unsubstituted nitrogen-containing heteroaryl group; Ar 1 and Ar 2 is represented as any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C10-C30 fused ring group.

16. The organic chiral auxiliary functional material according to claim 15, wherein has the following structure:

17. The preparation method of the organic chiral auxiliary functional material X according to claim 15, wherein, Its preparation includes: dissolving precursor M14 and raw material C in 1,4-dioxane, changing the gas 3 times, then adding tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stirring evenly, heating to reflux to obtain intermediate M15; the dosage ratio of precursor M14, raw material C, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; subsequently, dissolving intermediate M15 and raw material E in 1,4-dioxane, changing the gas 3 times, then adding tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stirring evenly, heating to reflux to obtain intermediate M16; the dosage ratio of precursor M15, raw material E, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; finally, dissolving intermediate M16 and raw material F in a mixed solvent of toluene, ethanol and water, changing the gas 3 times, then adding tetrakis(triphenylphosphine)palladium and potassium carbonate under nitrogen protection, stirring evenly, heating to reflux to obtain material X; the dosage ratio of intermediate M16, raw material F, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:2.5:0.01:5; The synthetic route is shown as follows:

18. The preparation method of the organic chiral auxiliary functional material XI according to claim 15, characterized in that, The preparation method includes: dissolving precursor M14 and raw material C in 1,4-dioxane, replacing the gas 3 times, then adding palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stirring evenly, and heating to reflux to obtain intermediate M15; the dosage ratio of the precursor M14, raw material C, palladium tetrakis(triphenylphosphine) and potassium carbonate is 1:2.5:0.01:5; subsequently, dissolving intermediate M15 and raw material G in 1,4-dioxane, replacing the gas 3 times, then adding palladium tetrakis(triphenylphosphine) and potassium carbonate under nitrogen protection, stirring evenly, and heating to reflux to obtain material XI; the dosage ratio of the precursor M15, raw material G, palladium tetrakis(triphenylphosphine) and potassium carbonate is 1:2.5:0.01:5; The synthetic route is as follows:

19. Use of an organic chiral auxiliary functional material according to any one of claims 1, 4, 8, 12 and 15 in the preparation of a circularly polarized organic electroluminescent device.

20. A circularly polarized organic light-emitting device, characterized in that, The circularly polarized organic light-emitting device includes a cathode, an anode, and an organic layer located between the cathode and the anode, and the organic layer includes the organic chiral auxiliary functional material according to any one of claims 1, 4, 8, 12 and 15.

21. The circularly polarized organic light emitting device according to claim 20, wherein The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, and an electron transport layer, and is characterized in that: any one of the organic chiral auxiliary functional materials according to any one of claims 1, 4, 8, 12 and 15 is used as the host material in the light-emitting layer of the device, or as the electron transport layer material, or as the hole transport layer material; Preferably, the luminescent material in the light-emitting layer is selected from Ir(bt)2acac, Ir(ppy)2acac, FIrpic), three TADF molecules (Ac-CNP, DMAC-BP, DMAC-DPS), and three d-f transition rare-earth luminescent complexes (CeTBO 2Et , EuI2-N8, Eu(Tp 2Et )2), etc.; the structural formulas of the above luminescent materials are shown as follows:

Images